Hydro­gen bonds and C—H...O interactions in 2,2′-dimethoxybiphenyl-5,5′-dimethanol at 150 K

The title compound, C₁₆H₁₈O₄, crystallized in the centrosymmetric space group P2₁/c with one mol­ecule in the asymmetric unit. The two hydroxyl-H atoms are ordered, and are involved in intermolecular hydrogen bonds with O_donor...O_acceptor distances of 2.761 (1) and 2.699 (1) Å, and O—H...O angles of 157 (2) and 168 (2)°. Seven leading intermolecular C—H...O interactions have H...O distances ranging from 2.41 to 2.76 Å and C—H...O angles ranging from 125 to 170°. The hydrogen bonds and C—H...O interactions form chain and ring patterns, resulting in a richly three-dimensional network. The bi­phenyl twist angle is 67.2 (1)°.

Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: TEXSAN (Molecular Structure Corporation, 1992-1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN and PLATON (Spek, 1990).

2,2'-dimethoxybiphenyl-5,5'-dimethanol

Crystal data

C16H18O4	F(000) = 584
Mr = 274.32	Dx = 1.336 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.4104 (2) Å	Cell parameters from 26987 reflections
b = 7.4078 (1) Å	θ = 1.9–27.5°
c = 16.9198 (3) Å	µ = 0.10 mm^−1
β = 107.473 (1)°	T = 150 K
V = 1364.17 (4) Å^3	Cut column, colorless
Z = 4	0.27 × 0.23 × 0.19 mm

Data collection

Nonius KappaCCD diffractometer	2471 reflections with I > 2σ(I)
Radiation source: X-ray tube	Rint = 0.042
Graphite monochromator	θmax = 27.5°
ω scans with κ offsets	h = −14→14
27579 measured reflections	k = −9→9
3137 independent reflections	l = −21→20

Refinement

Refinement on F^2	189 parameters
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.046	Weighting scheme based on measured s.u.'s w = 1/[σ^2cs + (0.026I)^2]
wR(F^2) = 0.099	(Δ/σ)max < 0.001
S = 1.99	Δρmax = 0.28 e Å^−3
3137 reflections	Δρmin = −0.31 e Å^−3

Special details

Experimental. The Laue group assignment, the systematic absences and the centrosymmetry indicated by the intensity statistics led to unique assignment of the space group as P2₁/c (No. 14); since refinement proceeded well, it was adopted. Fourier difference methods were used to locate initial H atom positions, and these H atoms were refined. Refined C—H distances ranged from 0.93 (1) to 1.03 (1) Å, with mean value 0.99 (3) Å; their U_iso values ranged from 0.9 to 1.5 times the U_eq values of the attached C atoms. The H atoms, excepting the hydroxyl H atoms, were then made canonical, with C—H = 0.98 Å and U_iso = 1.2 × U_eq of the attached C atom. In the later stages of refinement the extinction coefficient was predicted to be negligibly small, so was not included in the model. The maximum peak in the final difference map occurs ~0.2 Å from C3, the maximum negative peak ~0.8 Å from C2 and 1.2 Å from O1 and C3.

Geometry. Table of Least-Squares Planes ——————————

————– Plane number 1 —————

Atoms Defining Plane Distance e.s.d. C1 (1) 0.0177 0.0011 C2 (1) -0.0167 0.0011 C3 (1) -0.0009 0.0012 C4 (1) 0.0184 0.0012 C5 (1) -0.0136 0.0011 C6 (1) -0.0054 0.0011

Additional Atoms Distance O1 (1) -0.0991 O2 (1) 1.3731 C13 (1) -0.5661 C14 (1) 0.0234

Mean deviation from plane is 0.0121 angstroms Chi-squared: 961.8

————– Plane number 2 —————

Atoms Defining Plane Distance e.s.d. C7 (1) 0.0017 0.0011 C8 (1) 0.0086 0.0011 C9 (1) -0.0116 0.0012 C10 (1) 0.0009 0.0012 C11 (1) 0.0102 0.0012 C12 (1) -0.0115 0.0011

Additional Atoms Distance O3 (1) 0.0096 O4 (1) 0.9605 C15 (1) -0.0041 C16 (1) 0.0488

Mean deviation from plane is 0.0074 angstroms Chi-squared: 339.2

Dihedral angles between least-squares planes plane plane angle 2 1 112.83

————– Plane number 3 —————

Atoms Defining Plane Distance e.s.d. C1 (2) -0.0177 0.0011 C2 (2) 0.0167 0.0011 C3 (2) 0.0009 0.0012 C4 (2) -0.0184 0.0012 C5 (2) 0.0136 0.0011 C6 (2) 0.0054 0.0011

Mean deviation from plane is 0.0121 angstroms Chi-squared: 961.8

Dihedral angles between least-squares planes plane plane angle 3 1 48.82 3 2 67.46

————– Plane number 4 —————

Atoms Defining Plane Distance e.s.d. C7 (2) -0.0017 0.0011 C8 (2) -0.0086 0.0011 C9 (2) 0.0116 0.0012 C10 (2) -0.0009 0.0012 C11 (2) -0.0102 0.0012 C12 (2) 0.0115 0.0011

Mean deviation from plane is 0.0074 angstroms Chi-squared: 339.2

Dihedral angles between least-squares planes plane plane angle 4 1 67.46 4 2 137.86 4 3 112.83

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

	x	y	z	Uiso*/Ueq
O1	0.30374 (7)	0.2176 (1)	0.84047 (5)	0.0258 (2)
O2	−0.05028 (9)	−0.3299 (1)	0.93253 (6)	0.0366 (3)
O3	0.43676 (7)	−0.1431 (1)	0.89559 (5)	0.0294 (3)
O4	0.18529 (9)	−0.0792 (1)	0.51018 (5)	0.0313 (3)
C1	0.1921 (1)	−0.0542 (2)	0.81556 (7)	0.0197 (3)
C2	0.2081 (1)	0.1183 (2)	0.85151 (7)	0.0203 (3)
C3	0.1296 (1)	0.1828 (2)	0.89336 (8)	0.0241 (3)
C4	0.0315 (1)	0.0765 (2)	0.89818 (7)	0.0236 (3)
C5	0.0091 (1)	−0.0905 (2)	0.86006 (7)	0.0227 (3)
C6	0.0908 (1)	−0.1545 (2)	0.81941 (7)	0.0216 (3)
C7	0.2765 (1)	−0.1248 (2)	0.77038 (7)	0.0203 (3)
C8	0.3996 (1)	−0.1691 (2)	0.81157 (8)	0.0223 (3)
C9	0.4740 (1)	−0.2376 (2)	0.76727 (8)	0.0257 (3)
C10	0.4280 (1)	−0.2574 (2)	0.68193 (8)	0.0251 (4)
C11	0.3078 (1)	−0.2131 (2)	0.63939 (7)	0.0229 (3)
C12	0.2329 (1)	−0.1495 (2)	0.68524 (7)	0.0211 (3)
C13	0.2999 (1)	0.4082 (2)	0.85129 (9)	0.0343 (4)
C14	−0.0963 (1)	−0.2047 (2)	0.86661 (8)	0.0279 (4)
C15	0.5608 (1)	−0.1891 (2)	0.94011 (9)	0.0382 (4)
C16	0.2591 (1)	−0.2318 (2)	0.54662 (8)	0.0282 (4)
H1O2	−0.109 (2)	−0.405 (3)	0.937 (1)	0.070 (6)*
H1O4	0.108 (2)	−0.124 (2)	0.480 (1)	0.071 (6)*
H3	0.1429	0.3023	0.9194	0.029*
H4	−0.0228	0.1207	0.9292	0.028*
H6	0.0763	−0.2733	0.7928	0.026*
H9	0.5590	−0.2720	0.7962	0.031*
H10	0.4818	−0.3038	0.6511	0.030*
H12	0.1467	−0.1215	0.6563	0.025*
H13C	0.3127	0.4355	0.9099	0.041*
H13A	0.3648	0.4655	0.8330	0.041*
H13B	0.2197	0.4546	0.8183	0.041*
H14A	−0.1322	−0.2699	0.8146	0.034*
H14B	−0.1591	−0.1281	0.8783	0.034*
H15B	0.6171	−0.1223	0.9171	0.046*
H15C	0.5772	−0.1576	0.9987	0.046*
H15A	0.5732	−0.3190	0.9351	0.046*
H16A	0.3284	−0.2412	0.5239	0.034*
H16B	0.2090	−0.3414	0.5331	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0250 (5)	0.0190 (5)	0.0381 (5)	−0.0032 (4)	0.0165 (4)	−0.0014 (4)
O2	0.0368 (6)	0.0409 (6)	0.0312 (6)	−0.0157 (5)	0.0090 (4)	0.0072 (4)
O3	0.0243 (5)	0.0364 (5)	0.0254 (5)	0.0045 (4)	0.0042 (4)	0.0011 (4)
O4	0.0373 (6)	0.0288 (5)	0.0297 (5)	0.0091 (4)	0.0128 (4)	0.0015 (4)
C1	0.0199 (6)	0.0212 (6)	0.0182 (6)	0.0025 (5)	0.0061 (5)	0.0027 (5)
C2	0.0186 (6)	0.0206 (7)	0.0219 (6)	−0.0018 (5)	0.0063 (5)	0.0031 (5)
C3	0.0262 (7)	0.0216 (7)	0.0257 (7)	−0.0006 (5)	0.0097 (5)	−0.0014 (5)
C4	0.0233 (6)	0.0263 (7)	0.0235 (7)	0.0022 (5)	0.0106 (5)	0.0014 (5)
C5	0.0207 (6)	0.0249 (7)	0.0223 (7)	0.0002 (5)	0.0062 (5)	0.0033 (5)
C6	0.0229 (6)	0.0195 (6)	0.0227 (7)	−0.0008 (5)	0.0073 (5)	−0.0003 (5)
C7	0.0212 (6)	0.0160 (6)	0.0264 (7)	−0.0010 (5)	0.0112 (5)	0.0015 (5)
C8	0.0234 (7)	0.0182 (6)	0.0258 (7)	−0.0022 (5)	0.0080 (5)	0.0008 (5)
C9	0.0191 (6)	0.0240 (7)	0.0339 (8)	0.0015 (5)	0.0078 (5)	0.0014 (6)
C10	0.0242 (7)	0.0210 (7)	0.0345 (8)	0.0005 (5)	0.0154 (6)	−0.0015 (6)
C11	0.0251 (7)	0.0183 (6)	0.0282 (7)	−0.0007 (5)	0.0125 (6)	−0.0006 (5)
C12	0.0192 (6)	0.0180 (6)	0.0269 (7)	0.0003 (5)	0.0083 (5)	0.0005 (5)
C13	0.0368 (8)	0.0190 (7)	0.0533 (9)	−0.0036 (6)	0.0228 (7)	0.0007 (6)
C14	0.0249 (7)	0.0302 (7)	0.0316 (8)	−0.0035 (6)	0.0128 (6)	0.0002 (6)
C15	0.0287 (7)	0.0448 (9)	0.0351 (8)	0.0069 (6)	0.0006 (6)	0.0019 (7)
C16	0.0282 (7)	0.0281 (7)	0.0314 (8)	0.0065 (6)	0.0138 (6)	−0.0010 (6)

Geometric parameters (Å, º)

O1—C2	1.374 (1)	C7—C12	1.388 (2)
O1—C13	1.426 (2)	C8—C9	1.387 (2)
O2—C14	1.424 (2)	C9—C10	1.388 (2)
O2—H1O2	0.89 (2)	C9—H9	0.98
O3—C8	1.370 (1)	C10—C11	1.383 (2)
O3—C15	1.431 (2)	C10—H10	0.98
O4—C16	1.434 (2)	C11—C12	1.398 (2)
O4—H1O4	0.94 (2)	C11—C16	1.506 (2)
C1—C2	1.403 (2)	C12—H12	0.98
C1—C6	1.392 (2)	C13—H13C	0.98
C1—C7	1.492 (2)	C13—H13A	0.98
C2—C3	1.384 (2)	C13—H13B	0.98
C3—C4	1.391 (2)	C14—H14A	0.98
C3—H3	0.98	C14—H14B	0.98
C4—C5	1.383 (2)	C15—H15B	0.98
C4—H4	0.98	C15—H15C	0.98
C5—C6	1.396 (2)	C15—H15A	0.98
C5—C14	1.502 (2)	C16—H16A	0.98
C6—H6	0.98	C16—H16B	0.98
C7—C8	1.407 (2)
C2—O1—C13	117.17 (9)	C9—C10—H10	119.2
C14—O2—H1O2	111 (1)	C11—C10—H10	119.2
C8—O3—C15	117.5 (1)	C10—C11—C12	117.9 (1)
C16—O4—H1O4	107 (1)	C10—C11—C16	121.2 (1)
C2—C1—C6	117.9 (1)	C12—C11—C16	120.9 (1)
C2—C1—C7	121.4 (1)	C7—C12—C11	122.2 (1)
C6—C1—C7	120.7 (1)	C7—C12—H12	118.9
O1—C2—C1	115.7 (1)	C11—C12—H12	118.9
O1—C2—C3	123.2 (1)	O1—C13—H13C	109.5
C1—C2—C3	121.1 (1)	O1—C13—H13A	109.5
C2—C3—C4	119.4 (1)	O1—C13—H13B	109.5
C2—C3—H3	120.3	H13C—C13—H13A	109.5
C4—C3—H3	120.3	H13C—C13—H13B	109.5
C3—C4—C5	121.2 (1)	H13A—C13—H13B	109.5
C3—C4—H4	119.4	O2—C14—C5	108.0 (1)
C5—C4—H4	119.4	O2—C14—H14A	109.8
C4—C5—C6	118.5 (1)	O2—C14—H14B	109.8
C4—C5—C14	120.6 (1)	C5—C14—H14A	109.8
C6—C5—C14	120.9 (1)	C5—C14—H14B	109.8
C1—C6—C5	121.9 (1)	H14A—C14—H14B	109.5
C1—C6—H6	119.0	O3—C15—H15B	109.5
C5—C6—H6	119.1	O3—C15—H15C	109.5
C1—C7—C8	122.0 (1)	O3—C15—H15A	109.5
C1—C7—C12	119.5 (1)	H15B—C15—H15C	109.5
C8—C7—C12	118.5 (1)	H15B—C15—H15A	109.5
O3—C8—C7	115.7 (1)	H15C—C15—H15A	109.5
O3—C8—C9	124.3 (1)	O4—C16—C11	111.2 (1)
C7—C8—C9	120.0 (1)	O4—C16—H16A	109.0
C8—C9—C10	119.9 (1)	O4—C16—H16B	109.0
C8—C9—H9	120.0	C11—C16—H16A	109.1
C10—C9—H9	120.0	C11—C16—H16B	109.0
C9—C10—C11	121.5 (1)	H16A—C16—H16B	109.5
O1—C2—C1—C6	−175.0 (1)	C2—C3—C4—C5	−1.7 (2)
O1—C2—C1—C7	1.6 (2)	C3—C2—O1—C13	−18.3 (2)
O1—C2—C3—C4	176.9 (1)	C3—C2—C1—C6	3.4 (2)
O2—C14—C5—C4	−96.1 (1)	C3—C2—C1—C7	−180.0 (1)
O2—C14—C5—C6	80.3 (1)	C3—C4—C5—C6	2.8 (2)
O3—C8—C7—C1	−0.1 (2)	C3—C4—C5—C14	179.3 (1)
O3—C8—C7—C12	−179.4 (1)	C5—C6—C1—C7	−178.9 (1)
O3—C8—C9—C10	−179.4 (1)	C6—C1—C7—C8	−114.5 (1)
O4—C16—C11—C10	−137.3 (1)	C6—C1—C7—C12	64.9 (1)
O4—C16—C11—C12	42.4 (2)	C7—C8—O3—C15	179.1 (1)
C1—C2—O1—C13	160.2 (1)	C7—C8—C9—C10	1.9 (2)
C1—C2—C3—C4	−1.5 (2)	C7—C12—C11—C10	2.1 (2)
C1—C6—C5—C4	−0.8 (2)	C7—C12—C11—C16	−177.6 (1)
C1—C6—C5—C14	−177.2 (1)	C8—C7—C12—C11	−1.4 (2)
C1—C7—C8—C9	178.7 (1)	C8—C9—C10—C11	−1.1 (2)
C1—C7—C12—C11	179.2 (1)	C9—C8—O3—C15	0.3 (2)
C2—C1—C6—C5	−2.3 (2)	C9—C8—C7—C12	−0.7 (2)
C2—C1—C7—C8	69.0 (2)	C9—C10—C11—C12	−0.8 (2)
C2—C1—C7—C12	−111.6 (1)	C9—C10—C11—C16	178.9 (1)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O4^i	0.89 (2)	1.92 (2)	2.761 (1)	157 (2)
O4—H1O4···O2^ii	0.94 (2)	1.77 (2)	2.699 (1)	168 (2)
C10—H10···O1^iii	0.98	2.41	3.201 (1)	137
C3—H3···O4^iv	0.98	2.52	3.490 (1)	170
C12—H12···O2^v	0.98	2.67	3.380 (2)	129
C15—H15C···O1^vi	0.98	2.69	3.574 (2)	150
C4—H4···O2^vii	0.98	2.72	3.377 (2)	125
C14—H14A···O1^i	0.98	2.76	3.637 (2)	149
C13—H13C···O4^iv	0.98	2.76	3.557 (2)	139

Symmetry codes: (i) −x, y−1/2, −z+3/2; (ii) x, −y−1/2, z−1/2; (iii) −x+1, y−1/2, −z+3/2; (iv) x, −y+1/2, z+1/2; (v) −x, y+1/2, −z+3/2; (vi) −x+1, −y, −z+2; (vii) −x, −y, −z+2.