threo-2-(2,6-Di­methoxy­phenoxy)-1-(3,4-di­methoxy­phenyl)-1,3-propane­diol

In the crystals of the title compound, C₁₉H₂₄O₇, the mol­ecules adopt a conformation in which the torsion angle C(aryl)—C—C—O(aryl­oxy) is −70.5 (2)° and the torsion angle C(aryl)—O—C—C(benzyl­ic) is −148.25 (19)°. This leads to a closest C(aryl)...C(aryl) distance of 4.319 (3) Å. This distance is, within experimental error, identical to the calculated maximum value obtained when the torsion angle C(aryl)—O—C—C(benzyl­ic) is varied and the torsion angle C(aryl)—C—C—O(aryl­oxy) is kept constant. The angle between the aromatic ring planes is 75.79 (7)°. The hydrogen-bonding pattern reveals intramolecular interactions and formation of ribbons of mol­ecules, parallel to the a axis.

Key indicators

• Single-crystal X-ray study
• T = 183 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.051
• wR factor = 0.123
• Data-to-parameter ratio = 12.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT and SADABS (Sheldrick, 2001); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2000); software used to prepare material for publication: SHELXTL.

threo-2-(2,6-dimethoxyphenoxy)-1-(3,4-dimethoxyphenyl)-1,3-propanediol

Crystal data

C19H24O7	F(000) = 388
Mr = 364.38	Dx = 1.370 Mg m^−3
Triclinic, P1	Melting point: 383–385 k K
a = 6.1632 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1891 (3) Å	Cell parameters from 3859 reflections
c = 15.9231 (5) Å	θ = 2.3–25.4°
α = 98.913 (1)°	µ = 0.10 mm^−1
β = 90.664 (1)°	T = 183 K
γ = 97.328 (1)°	Plate, colourless
V = 883.17 (5) Å^3	0.25 × 0.10 × 0.02 mm
Z = 2

Data collection

Siemens SMART CCD diffractometer	3238 independent reflections
Radiation source: fine-focus sealed tube	2141 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
ω scans	θmax = 25.4°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −7→7
Tmin = 0.974, Tmax = 0.998	k = −11→11
9676 measured reflections	l = −19→19

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0549P)^2 + 0.2595P] where P = (Fo^2 + 2Fc^2)/3
3238 reflections	(Δ/σ)max < 0.001
265 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

Experimental. Data were collected at 183 K using a Siemens SMART CCD diffractometer equipped with a Siemens LT-2 A low temperature device. A full sphere of reciprocal space was scanned by 0.3° steps in ω with a crystal–to–detector distance of 3.97 cm, 30 s per frame. Preliminary orientation matrix was obtained from the first 100 frames using SMART (Siemens, 1995). The collected frames were integrated using the preliminary orientation matrix which was updated every 100 frames. Final cell parameters were obtained by refinement on the position of 3859 reflections with I>10σ(I) after integration of all the frames data using SAINT (Siemens, 1995).

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.

The data were empirically corrected for absorption and other effects using SADABS (Sheldrick, 2001) based on the method of Blessing (1995). The structure was solved by direct methods and refined by full-matrix least squares on all F² data using SHELXTL (Bruker, 1997). All non-H atoms were refined anisotropically.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.6522 (3)	0.14298 (18)	0.43995 (10)	0.0314 (4)
O2	0.3351 (3)	0.27379 (18)	0.50668 (10)	0.0308 (4)
O4	0.4691 (3)	0.4288 (2)	0.12904 (10)	0.0311 (4)
H4	0.4852	0.5220	0.1346	0.055 (10)*
O5	1.0232 (3)	0.36028 (18)	0.08185 (11)	0.0327 (4)
H5	1.1551	0.3630	0.0968	0.078 (13)*
O6	0.7514 (3)	0.63594 (17)	0.22359 (10)	0.0246 (4)
O7	0.5561 (3)	0.75577 (19)	0.10900 (11)	0.0357 (5)
O8	1.1417 (3)	0.75625 (19)	0.29620 (10)	0.0316 (4)
C1	0.5385 (4)	0.3545 (2)	0.26737 (14)	0.0225 (5)
C2	0.6366 (4)	0.2583 (2)	0.31201 (15)	0.0232 (5)
H2	0.7522	0.2091	0.2871	0.024 (6)*
C3	0.5677 (4)	0.2342 (2)	0.39138 (15)	0.0222 (5)
C4	0.3942 (4)	0.3062 (3)	0.42818 (15)	0.0239 (6)
C5	0.2975 (4)	0.3999 (3)	0.38396 (15)	0.0276 (6)
H5A	0.1801	0.4480	0.4080	0.031 (7)*
C6	0.3707 (4)	0.4245 (3)	0.30421 (15)	0.0266 (6)
H6	0.3038	0.4904	0.2749	0.028 (7)*
C7	0.8202 (4)	0.0615 (3)	0.40389 (17)	0.0320 (6)
H7A	0.7692	0.0054	0.3482	0.028 (7)*
H7B	0.8556	−0.0074	0.4416	0.036 (7)*
H7C	0.9512	0.1307	0.3970	0.045 (8)*
C8	0.1777 (4)	0.3569 (3)	0.55063 (16)	0.0339 (7)
H8A	0.2278	0.4634	0.5546	0.036 (7)*
H8B	0.1611	0.3314	0.6079	0.048 (8)*
H8C	0.0365	0.3327	0.5194	0.045 (8)*
C9	0.6282 (4)	0.3826 (3)	0.18235 (15)	0.0236 (5)
H9	0.6702	0.2868	0.1524	0.021 (6)*
C10	0.8333 (4)	0.4970 (2)	0.19224 (15)	0.0231 (5)
H10	0.9346	0.4735	0.2363	0.013 (5)*
C11	0.9529 (4)	0.5015 (3)	0.10974 (16)	0.0279 (6)
H11A	0.8544	0.5257	0.0658	0.025 (6)*
H11B	1.0811	0.5795	0.1187	0.025 (6)*
C12	0.8552 (4)	0.7668 (2)	0.20159 (14)	0.0236 (5)
C13	0.7491 (4)	0.8344 (3)	0.14312 (15)	0.0285 (6)
C14	0.8424 (5)	0.9714 (3)	0.12468 (17)	0.0360 (7)
H14	0.7725	1.0186	0.0848	0.041 (8)*
C15	1.0373 (5)	1.0381 (3)	0.16485 (17)	0.0369 (7)
H15	1.0991	1.1323	0.1527	0.041 (7)*
C16	1.1461 (4)	0.9718 (3)	0.22248 (17)	0.0335 (6)
H16	1.2811	1.0193	0.2489	0.036 (7)*
C17	1.0536 (4)	0.8346 (3)	0.24077 (15)	0.0260 (6)
C18	0.4469 (5)	0.8156 (3)	0.04459 (18)	0.0431 (7)
H18A	0.4119	0.9146	0.0680	0.051 (9)*
H18B	0.3115	0.7502	0.0254	0.056 (9)*
H18C	0.5427	0.8229	−0.0037	0.057 (9)*
C19	1.3403 (4)	0.8243 (3)	0.34151 (18)	0.0400 (7)
H19A	1.4571	0.8377	0.3011	0.048 (8)*
H19B	1.3819	0.7606	0.3813	0.045 (8)*
H19C	1.3178	0.9213	0.3731	0.052 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0360 (11)	0.0308 (10)	0.0317 (10)	0.0134 (8)	0.0071 (8)	0.0099 (8)
O2	0.0332 (10)	0.0331 (10)	0.0283 (10)	0.0089 (8)	0.0126 (8)	0.0075 (8)
O4	0.0271 (10)	0.0346 (11)	0.0320 (10)	0.0021 (8)	−0.0045 (8)	0.0081 (8)
O5	0.0287 (11)	0.0276 (10)	0.0426 (11)	0.0089 (8)	0.0054 (9)	0.0040 (8)
O6	0.0223 (9)	0.0213 (9)	0.0307 (9)	0.0029 (7)	0.0051 (7)	0.0052 (7)
O7	0.0331 (11)	0.0357 (10)	0.0401 (11)	0.0057 (8)	−0.0100 (8)	0.0114 (8)
O8	0.0249 (10)	0.0339 (10)	0.0353 (10)	−0.0018 (8)	−0.0043 (8)	0.0082 (8)
C1	0.0217 (13)	0.0171 (12)	0.0273 (13)	−0.0020 (10)	0.0021 (10)	0.0026 (10)
C2	0.0176 (13)	0.0205 (12)	0.0309 (14)	0.0031 (10)	0.0045 (10)	0.0014 (10)
C3	0.0220 (13)	0.0171 (11)	0.0270 (13)	0.0016 (10)	−0.0014 (10)	0.0032 (10)
C4	0.0218 (13)	0.0231 (13)	0.0253 (13)	−0.0005 (11)	0.0040 (10)	0.0018 (10)
C5	0.0191 (13)	0.0305 (14)	0.0338 (15)	0.0065 (11)	0.0069 (11)	0.0033 (11)
C6	0.0232 (13)	0.0238 (13)	0.0343 (15)	0.0054 (11)	0.0003 (11)	0.0080 (11)
C7	0.0298 (15)	0.0287 (14)	0.0392 (16)	0.0129 (12)	−0.0015 (12)	0.0032 (12)
C8	0.0330 (16)	0.0356 (16)	0.0306 (15)	0.0022 (13)	0.0101 (12)	−0.0016 (12)
C9	0.0223 (13)	0.0215 (13)	0.0276 (13)	0.0037 (10)	0.0030 (10)	0.0049 (10)
C10	0.0218 (13)	0.0214 (12)	0.0280 (13)	0.0057 (10)	0.0028 (10)	0.0075 (10)
C11	0.0270 (14)	0.0239 (13)	0.0359 (15)	0.0082 (11)	0.0068 (11)	0.0099 (11)
C12	0.0245 (13)	0.0206 (13)	0.0257 (13)	0.0031 (11)	0.0055 (11)	0.0028 (10)
C13	0.0302 (15)	0.0267 (14)	0.0294 (14)	0.0083 (12)	0.0023 (11)	0.0027 (11)
C14	0.0445 (18)	0.0280 (15)	0.0393 (16)	0.0123 (13)	0.0043 (13)	0.0105 (12)
C15	0.0472 (18)	0.0193 (13)	0.0461 (17)	0.0040 (12)	0.0124 (14)	0.0102 (12)
C16	0.0325 (16)	0.0248 (14)	0.0408 (16)	−0.0011 (12)	0.0090 (13)	0.0016 (12)
C17	0.0282 (14)	0.0236 (13)	0.0263 (14)	0.0053 (11)	0.0054 (11)	0.0024 (10)
C18	0.0461 (19)	0.0488 (19)	0.0379 (17)	0.0147 (16)	−0.0060 (14)	0.0118 (14)
C19	0.0299 (16)	0.0437 (17)	0.0431 (17)	−0.0031 (13)	−0.0079 (14)	0.0035 (14)

Geometric parameters (Å, º)

O1—C3	1.369 (3)	C7—H7C	0.980
O1—C7	1.429 (3)	C8—H8A	0.980
O2—C4	1.372 (3)	C8—H8B	0.980
O2—C8	1.433 (3)	C8—H8C	0.980
O4—C9	1.436 (3)	C9—C10	1.528 (3)
O4—H4	0.840	C9—H9	1.0000
O5—C11	1.428 (3)	C10—C11	1.517 (3)
O5—H5	0.840	C10—H10	1.000
O6—C12	1.384 (3)	C11—H11A	0.990
O6—C10	1.451 (3)	C11—H11B	0.990
O7—C13	1.370 (3)	C12—C17	1.393 (3)
O7—C18	1.436 (3)	C12—C13	1.396 (3)
O8—C17	1.370 (3)	C13—C14	1.391 (4)
O8—C19	1.433 (3)	C14—C15	1.379 (4)
C1—C6	1.376 (3)	C14—H14	0.950
C1—C2	1.404 (3)	C15—C16	1.387 (4)
C1—C9	1.515 (3)	C15—H15	0.950
C2—C3	1.379 (3)	C16—C17	1.391 (3)
C2—H2	0.950	C16—H16	0.9500
C3—C4	1.414 (3)	C18—H18A	0.980
C4—C5	1.378 (3)	C18—H18B	0.980
C5—C6	1.394 (3)	C18—H18C	0.980
C5—H5A	0.950	C19—H19A	0.980
C6—H6	0.950	C19—H19B	0.980
C7—H7A	0.980	C19—H19C	0.980
C7—H7B	0.980
C3—O1—C7	117.13 (18)	O6—C10—C9	103.73 (17)
C4—O2—C8	117.26 (19)	O6—C10—C11	112.67 (17)
C9—O4—H4	109.5	C9—C10—C11	112.66 (19)
C11—O5—H5	109.5	O6—C10—H10	109.2
C12—O6—C10	119.21 (17)	C9—C10—H10	109.2
C13—O7—C18	117.1 (2)	C11—C10—H10	109.2
C17—O8—C19	117.2 (2)	O5—C11—C10	109.38 (18)
C6—C1—C2	118.7 (2)	O5—C11—H11A	109.8
C6—C1—C9	122.5 (2)	C10—C11—H11A	109.8
C2—C1—C9	118.7 (2)	O5—C11—H11B	109.8
C3—C2—C1	121.0 (2)	C10—C11—H11B	109.8
C3—C2—H2	119.5	H11A—C11—H11B	108.2
C1—C2—H2	119.5	O6—C12—C17	121.0 (2)
O1—C3—C2	125.6 (2)	O6—C12—C13	118.3 (2)
O1—C3—C4	114.8 (2)	C17—C12—C13	120.6 (2)
C2—C3—C4	119.6 (2)	O7—C13—C12	114.7 (2)
O2—C4—C5	125.4 (2)	O7—C13—C14	125.9 (2)
O2—C4—C3	115.4 (2)	C12—C13—C14	119.4 (2)
C5—C4—C3	119.2 (2)	C15—C14—C13	119.3 (2)
C4—C5—C6	120.5 (2)	C15—C14—H14	120.3
C4—C5—H5A	119.7	C13—C14—H14	120.3
C6—C5—H5A	119.7	C14—C15—C16	122.1 (2)
C1—C6—C5	120.9 (2)	C14—C15—H15	119.0
C1—C6—H6	119.6	C16—C15—H15	119.0
C5—C6—H6	119.6	C17—C16—C15	118.7 (3)
O1—C7—H7A	109.5	C17—C16—H16	120.6
O1—C7—H7B	109.5	C15—C16—H16	120.6
H7A—C7—H7B	109.5	O8—C17—C12	114.9 (2)
O1—C7—H7C	109.5	O8—C17—C16	125.2 (2)
H7A—C7—H7C	109.5	C12—C17—C16	119.9 (2)
H7B—C7—H7C	109.5	O7—C18—H18A	109.5
O2—C8—H8A	109.5	O7—C18—H18B	109.5
O2—C8—H8B	109.5	H18A—C18—H18B	109.5
H8A—C8—H8B	109.5	O7—C18—H18C	109.5
O2—C8—H8C	109.5	H18A—C18—H18C	109.5
H8A—C8—H8C	109.5	H18B—C18—H18C	109.5
H8B—C8—H8C	109.5	O8—C19—H19A	109.5
O4—C9—C1	112.49 (19)	O8—C19—H19B	109.5
O4—C9—C10	109.19 (18)	H19A—C19—H19B	109.5
C1—C9—C10	112.22 (19)	O8—C19—H19C	109.5
O4—C9—H9	107.6	H19A—C19—H19C	109.5
C1—C9—H9	107.6	H19B—C19—H19C	109.5
C10—C9—H9	107.6
C6—C1—C2—C3	−0.2 (3)	O4—C9—C10—C11	−67.2 (2)
C9—C1—C2—C3	177.0 (2)	C1—C9—C10—C11	167.35 (19)
C7—O1—C3—C2	−2.5 (3)	O6—C10—C11—O5	−178.47 (19)
C7—O1—C3—C4	176.9 (2)	C9—C10—C11—O5	−61.5 (3)
C1—C2—C3—O1	180.0 (2)	C10—O6—C12—C17	−76.6 (3)
C1—C2—C3—C4	0.6 (3)	C10—O6—C12—C13	107.6 (2)
C8—O2—C4—C5	−7.7 (3)	C18—O7—C13—C12	−176.2 (2)
C8—O2—C4—C3	173.0 (2)	C18—O7—C13—C14	4.1 (4)
O1—C3—C4—O2	−0.3 (3)	O6—C12—C13—O7	−4.4 (3)
C2—C3—C4—O2	179.1 (2)	C17—C12—C13—O7	179.7 (2)
O1—C3—C4—C5	−179.7 (2)	O6—C12—C13—C14	175.3 (2)
C2—C3—C4—C5	−0.2 (3)	C17—C12—C13—C14	−0.5 (4)
O2—C4—C5—C6	−179.8 (2)	O7—C13—C14—C15	179.4 (2)
C3—C4—C5—C6	−0.5 (3)	C12—C13—C14—C15	−0.3 (4)
C2—C1—C6—C5	−0.5 (3)	C13—C14—C15—C16	1.0 (4)
C9—C1—C6—C5	−177.7 (2)	C14—C15—C16—C17	−0.7 (4)
C4—C5—C6—C1	0.9 (4)	C19—O8—C17—C12	−177.0 (2)
C6—C1—C9—O4	−26.8 (3)	C19—O8—C17—C16	2.8 (3)
C2—C1—C9—O4	156.1 (2)	O6—C12—C17—O8	4.8 (3)
C6—C1—C9—C10	96.8 (3)	C13—C12—C17—O8	−179.4 (2)
C2—C1—C9—C10	−80.3 (3)	O6—C12—C17—C16	−174.9 (2)
C12—O6—C10—C9	−148.25 (19)	C13—C12—C17—C16	0.8 (3)
C12—O6—C10—C11	−26.1 (3)	C15—C16—C17—O8	−179.9 (2)
O4—C9—C10—O6	54.9 (2)	C15—C16—C17—C12	−0.2 (4)
C1—C9—C10—O6	−70.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O6	0.84	2.20	2.669 (2)	115
O4—H4···O7	0.84	2.24	3.051 (2)	163
O5—H5···O4^i	0.84	1.99	2.807 (2)	164
C8—H8B···O8^ii	0.98	2.55	3.359 (3)	139
C9—H9···O5	1.00	2.52	2.940 (3)	105
C19—H19B···O2^iii	0.98	2.56	3.418 (3)	146

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