2,2-Dimethyl-5-(2,3,4-trimeth-oxy-benzyl-idene)-1,3-dioxane-4,6-dione.

The title compound, C(16)H(18)O(7), was prepared by the reaction of 2,2-dimethyl-1,3-dioxane-4,6-dione and 2,3,4-trimeth-oxy-benzaldehyde. The 1,3-dioxane ring is in a slightly distorted boat conformation. The crystal structure is stabilized by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For related structures, see: Zeng (2011a ▶,b ▶).

Experimental

Crystal data

C16H18O7

M = 322.30

Monoclinic,

a = 12.722 (3) Å

b = 9.2669 (19) Å

c = 13.537 (3) Å

β = 98.83 (3)°

V = 1577.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.22 × 0.18 × 0.16 mm

Data collection

Bruker SMART CCD diffractometer

14870 measured reflections

3613 independent reflections

3073 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.131

S = 1.03

3613 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811026201/lh5270sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026201/lh5270Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811026201/lh5270Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H18O7	F(000) = 680
Mr = 322.30	Dx = 1.358 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3073 reflections
a = 12.722 (3) Å	θ = 3.0–27.5°
b = 9.2669 (19) Å	µ = 0.11 mm−1
c = 13.537 (3) Å	T = 293 K
β = 98.83 (3)°	Block, yellow
V = 1577.0 (5) Å3	0.22 × 0.18 × 0.16 mm
Z = 4

Bruker SMART CCD diffractometer	3073 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
graphite	θmax = 27.5°, θmin = 3.0°
φ and ω scans	h = −16→16
14870 measured reflections	k = −12→10
3613 independent reflections	l = −17→17

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0828P)2 + 0.1973P] where P = (Fo2 + 2Fc2)/3
3613 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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.

	x	y	z	Uiso*/Ueq
O2	0.52394 (8)	0.12332 (10)	0.25642 (7)	0.0477 (2)
O3	0.30226 (7)	0.11922 (11)	0.24083 (6)	0.0475 (2)
O7	0.01954 (7)	0.41504 (10)	−0.11404 (7)	0.0455 (2)
O5	−0.04628 (7)	0.11016 (11)	0.07142 (6)	0.0470 (2)
O6	−0.09078 (7)	0.23104 (10)	−0.06837 (6)	0.0423 (2)
O4	0.17489 (8)	0.46436 (11)	−0.02499 (9)	0.0549 (3)
O1	0.61501 (7)	0.18353 (12)	0.09474 (8)	0.0535 (3)
C14	0.10299 (10)	0.38024 (13)	−0.04308 (9)	0.0390 (3)
C9	0.35150 (10)	0.14559 (12)	0.15946 (9)	0.0373 (3)
C13	0.09149 (9)	0.24390 (13)	0.01095 (8)	0.0361 (3)
C12	−0.01832 (9)	0.18810 (13)	0.00905 (8)	0.0361 (3)
C8	0.46155 (10)	0.14555 (13)	0.16543 (9)	0.0387 (3)
C4	0.28552 (10)	0.18482 (13)	0.07028 (9)	0.0390 (3)
C7	0.50721 (10)	0.18263 (13)	0.08077 (10)	0.0413 (3)
C6	0.44249 (11)	0.21837 (16)	−0.00816 (10)	0.0467 (3)
H6A	0.4726	0.2408	−0.0647	0.056*
C5	0.33352 (11)	0.22040 (15)	−0.01229 (10)	0.0455 (3)
H5A	0.2910	0.2462	−0.0718	0.055*
C10	0.17081 (10)	0.17055 (14)	0.06602 (9)	0.0395 (3)
H10A	0.1493	0.1002	0.1076	0.047*
C11	−0.05435 (10)	0.30305 (14)	−0.15114 (9)	0.0414 (3)
C15	−0.15002 (13)	0.37887 (18)	−0.20694 (12)	0.0561 (4)
H15A	−0.1781	0.4445	−0.1628	0.084*
H15B	−0.2033	0.3090	−0.2316	0.084*
H15C	−0.1296	0.4315	−0.2621	0.084*
C3	0.32531 (14)	−0.01527 (18)	0.29164 (13)	0.0626 (4)
H3A	0.2861	−0.0216	0.3467	0.094*
H3B	0.4001	−0.0210	0.3162	0.094*
H3C	0.3052	−0.0934	0.2461	0.094*
C2	0.58511 (12)	−0.00798 (17)	0.26325 (14)	0.0616 (4)
H2A	0.6262	−0.0156	0.3287	0.092*
H2B	0.6320	−0.0068	0.2141	0.092*
H2C	0.5379	−0.0891	0.2515	0.092*
C16	−0.00279 (14)	0.19646 (17)	−0.21299 (10)	0.0563 (4)
H16A	0.0574	0.1530	−0.1724	0.084*
H16B	0.0203	0.2456	−0.2683	0.084*
H16C	−0.0532	0.1230	−0.2377	0.084*
C1	0.66751 (13)	0.2140 (2)	0.01138 (14)	0.0695 (5)
H1A	0.7431	0.2112	0.0321	0.104*
H1B	0.6471	0.3082	−0.0143	0.104*
H1C	0.6476	0.1432	−0.0399	0.104*

	U11	U22	U33	U12	U13	U23
O2	0.0458 (5)	0.0472 (5)	0.0461 (5)	−0.0004 (4)	−0.0054 (4)	0.0007 (4)
O3	0.0486 (5)	0.0564 (6)	0.0394 (5)	0.0052 (4)	0.0130 (4)	0.0080 (4)
O7	0.0446 (5)	0.0398 (5)	0.0518 (5)	0.0001 (4)	0.0062 (4)	0.0080 (4)
O5	0.0473 (5)	0.0564 (5)	0.0399 (5)	−0.0060 (4)	0.0141 (4)	0.0081 (4)
O6	0.0350 (4)	0.0527 (5)	0.0392 (4)	−0.0028 (4)	0.0058 (3)	0.0051 (4)
O4	0.0456 (5)	0.0437 (5)	0.0765 (7)	−0.0090 (4)	0.0134 (5)	−0.0020 (5)
O1	0.0344 (5)	0.0634 (6)	0.0636 (6)	−0.0038 (4)	0.0109 (4)	−0.0018 (5)
C14	0.0361 (6)	0.0377 (6)	0.0455 (6)	0.0008 (5)	0.0134 (5)	−0.0020 (5)
C9	0.0402 (6)	0.0364 (6)	0.0360 (6)	−0.0007 (5)	0.0082 (5)	−0.0009 (4)
C13	0.0350 (6)	0.0407 (6)	0.0336 (5)	−0.0019 (4)	0.0082 (4)	−0.0017 (4)
C12	0.0356 (6)	0.0412 (6)	0.0329 (5)	−0.0005 (4)	0.0096 (4)	−0.0022 (4)
C8	0.0385 (6)	0.0352 (6)	0.0408 (6)	−0.0010 (5)	0.0012 (5)	−0.0018 (4)
C4	0.0358 (6)	0.0426 (6)	0.0389 (6)	0.0011 (5)	0.0072 (5)	0.0003 (5)
C7	0.0359 (6)	0.0390 (6)	0.0499 (7)	−0.0017 (5)	0.0097 (5)	−0.0046 (5)
C6	0.0438 (7)	0.0554 (7)	0.0435 (7)	0.0023 (6)	0.0149 (5)	0.0022 (6)
C5	0.0421 (7)	0.0567 (8)	0.0381 (6)	0.0051 (6)	0.0072 (5)	0.0042 (5)
C10	0.0390 (6)	0.0454 (6)	0.0349 (5)	−0.0004 (5)	0.0079 (5)	0.0008 (5)
C11	0.0442 (7)	0.0437 (6)	0.0364 (6)	−0.0003 (5)	0.0063 (5)	0.0044 (5)
C15	0.0520 (8)	0.0605 (9)	0.0524 (8)	0.0052 (6)	−0.0034 (6)	0.0089 (6)
C3	0.0726 (10)	0.0571 (9)	0.0623 (9)	−0.0038 (7)	0.0240 (8)	0.0149 (7)
C2	0.0482 (8)	0.0536 (8)	0.0775 (10)	0.0039 (6)	−0.0074 (7)	0.0128 (7)
C16	0.0732 (10)	0.0582 (8)	0.0390 (6)	0.0102 (7)	0.0131 (6)	0.0002 (6)
C1	0.0452 (8)	0.0925 (13)	0.0762 (11)	−0.0078 (8)	0.0267 (8)	−0.0085 (9)

O2—C8	1.3745 (15)	C6—C5	1.3789 (19)
O2—C2	1.4396 (18)	C6—H6A	0.9300
O3—C9	1.3702 (14)	C5—H5A	0.9300
O3—C3	1.4319 (18)	C10—H10A	0.9300
O7—C14	1.3567 (16)	C11—C15	1.5044 (19)
O7—C11	1.4379 (16)	C11—C16	1.5085 (19)
O5—C12	1.2056 (14)	C15—H15A	0.9600
O6—C12	1.3453 (15)	C15—H15B	0.9600
O6—C11	1.4406 (14)	C15—H15C	0.9600
O4—C14	1.1981 (15)	C3—H3A	0.9600
O1—C7	1.3553 (15)	C3—H3B	0.9600
O1—C1	1.4251 (19)	C3—H3C	0.9600
C14—C13	1.4783 (17)	C2—H2A	0.9600
C9—C8	1.3898 (17)	C2—H2B	0.9600
C9—C4	1.4082 (17)	C2—H2C	0.9600
C13—C10	1.3436 (17)	C16—H16A	0.9600
C13—C12	1.4861 (16)	C16—H16B	0.9600
C8—C7	1.4048 (18)	C16—H16C	0.9600
C4—C5	1.3931 (17)	C1—H1A	0.9600
C4—C10	1.4576 (17)	C1—H1B	0.9600
C7—C6	1.3901 (19)	C1—H1C	0.9600
C8—O2—C2	114.60 (11)	O7—C11—C15	105.86 (11)
C9—O3—C3	117.14 (11)	O6—C11—C15	105.95 (11)
C14—O7—C11	118.31 (10)	O7—C11—C16	110.48 (11)
C12—O6—C11	118.63 (9)	O6—C11—C16	110.34 (11)
C7—O1—C1	118.55 (12)	C15—C11—C16	114.48 (12)
O4—C14—O7	118.68 (12)	C11—C15—H15A	109.5
O4—C14—C13	125.83 (12)	C11—C15—H15B	109.5
O7—C14—C13	115.29 (10)	H15A—C15—H15B	109.5
O3—C9—C8	122.28 (11)	C11—C15—H15C	109.5
O3—C9—C4	116.70 (11)	H15A—C15—H15C	109.5
C8—C9—C4	120.82 (11)	H15B—C15—H15C	109.5
C10—C13—C14	125.73 (11)	O3—C3—H3A	109.5
C10—C13—C12	117.23 (11)	O3—C3—H3B	109.5
C14—C13—C12	116.94 (10)	H3A—C3—H3B	109.5
O5—C12—O6	118.84 (11)	O3—C3—H3C	109.5
O5—C12—C13	125.03 (11)	H3A—C3—H3C	109.5
O6—C12—C13	116.13 (10)	H3B—C3—H3C	109.5
O2—C8—C9	119.34 (11)	O2—C2—H2A	109.5
O2—C8—C7	120.90 (11)	O2—C2—H2B	109.5
C9—C8—C7	119.44 (11)	H2A—C2—H2B	109.5
C5—C4—C9	118.16 (11)	O2—C2—H2C	109.5
C5—C4—C10	123.32 (12)	H2A—C2—H2C	109.5
C9—C4—C10	118.16 (11)	H2B—C2—H2C	109.5
O1—C7—C6	124.85 (12)	C11—C16—H16A	109.5
O1—C7—C8	115.09 (12)	C11—C16—H16B	109.5
C6—C7—C8	120.04 (11)	H16A—C16—H16B	109.5
C5—C6—C7	119.77 (12)	C11—C16—H16C	109.5
C5—C6—H6A	120.1	H16A—C16—H16C	109.5
C7—C6—H6A	120.1	H16B—C16—H16C	109.5
C6—C5—C4	121.74 (12)	O1—C1—H1A	109.5
C6—C5—H5A	119.1	O1—C1—H1B	109.5
C4—C5—H5A	119.1	H1A—C1—H1B	109.5
C13—C10—C4	129.65 (11)	O1—C1—H1C	109.5
C13—C10—H10A	115.2	H1A—C1—H1C	109.5
C4—C10—H10A	115.2	H1B—C1—H1C	109.5
O7—C11—O6	109.50 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O4i	0.96	2.46	3.392 (2)	163
C16—H16B···O5ii	0.96	2.58	3.397 (2)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O4i	0.96	2.46	3.392 (2)	163
C16—H16B⋯O5ii	0.96	2.58	3.397 (2)	143

Symmetry codes: (i) ; (ii) .