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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 Odonor...Oacceptor 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)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100002900/fr1262sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100002900/fr1262Isup2.hkl
Contains datablock I

Computing details top

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 top
Crystal data top
C16H18O4F(000) = 584
Mr = 274.32Dx = 1.336 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.4104 (2) ÅCell parameters from 26987 reflections
b = 7.4078 (1) Åθ = 1.9–27.5°
c = 16.9198 (3) ŵ = 0.10 mm1
β = 107.473 (1)°T = 150 K
V = 1364.17 (4) Å3Cut column, colorless
Z = 40.27 × 0.23 × 0.19 mm
Data collection top
Nonius KappaCCD
diffractometer
2471 reflections with I > 2σ(I)
Radiation source: X-ray tubeRint = 0.042
Graphite monochromatorθmax = 27.5°
ω scans with κ offsetsh = 1414
27579 measured reflectionsk = 99
3137 independent reflectionsl = 2120
Refinement top
Refinement on F2189 parameters
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.046Weighting scheme based on measured s.u.'s w = 1/[σ2cs + (0.026I)2]
wR(F2) = 0.099(Δ/σ)max < 0.001
S = 1.99Δρmax = 0.28 e Å3
3137 reflectionsΔρmin = 0.31 e Å3
Special details top

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 Uiso values ranged from 0.9 to 1.5 times the Ueq 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 Uiso = 1.2 × Ueq 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 (Å2) top
xyzUiso*/Ueq
O10.30374 (7)0.2176 (1)0.84047 (5)0.0258 (2)
O20.05028 (9)0.3299 (1)0.93253 (6)0.0366 (3)
O30.43676 (7)0.1431 (1)0.89559 (5)0.0294 (3)
O40.18529 (9)0.0792 (1)0.51018 (5)0.0313 (3)
C10.1921 (1)0.0542 (2)0.81556 (7)0.0197 (3)
C20.2081 (1)0.1183 (2)0.85151 (7)0.0203 (3)
C30.1296 (1)0.1828 (2)0.89336 (8)0.0241 (3)
C40.0315 (1)0.0765 (2)0.89818 (7)0.0236 (3)
C50.0091 (1)0.0905 (2)0.86006 (7)0.0227 (3)
C60.0908 (1)0.1545 (2)0.81941 (7)0.0216 (3)
C70.2765 (1)0.1248 (2)0.77038 (7)0.0203 (3)
C80.3996 (1)0.1691 (2)0.81157 (8)0.0223 (3)
C90.4740 (1)0.2376 (2)0.76727 (8)0.0257 (3)
C100.4280 (1)0.2574 (2)0.68193 (8)0.0251 (4)
C110.3078 (1)0.2131 (2)0.63939 (7)0.0229 (3)
C120.2329 (1)0.1495 (2)0.68524 (7)0.0211 (3)
C130.2999 (1)0.4082 (2)0.85129 (9)0.0343 (4)
C140.0963 (1)0.2047 (2)0.86661 (8)0.0279 (4)
C150.5608 (1)0.1891 (2)0.94011 (9)0.0382 (4)
C160.2591 (1)0.2318 (2)0.54662 (8)0.0282 (4)
H1O20.109 (2)0.405 (3)0.937 (1)0.070 (6)*
H1O40.108 (2)0.124 (2)0.480 (1)0.071 (6)*
H30.14290.30230.91940.029*
H40.02280.12070.92920.028*
H60.07630.27330.79280.026*
H90.55900.27200.79620.031*
H100.48180.30380.65110.030*
H120.14670.12150.65630.025*
H13C0.31270.43550.90990.041*
H13A0.36480.46550.83300.041*
H13B0.21970.45460.81830.041*
H14A0.13220.26990.81460.034*
H14B0.15910.12810.87830.034*
H15B0.61710.12230.91710.046*
H15C0.57720.15760.99870.046*
H15A0.57320.31900.93510.046*
H16A0.32840.24120.52390.034*
H16B0.20900.34140.53310.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0250 (5)0.0190 (5)0.0381 (5)0.0032 (4)0.0165 (4)0.0014 (4)
O20.0368 (6)0.0409 (6)0.0312 (6)0.0157 (5)0.0090 (4)0.0072 (4)
O30.0243 (5)0.0364 (5)0.0254 (5)0.0045 (4)0.0042 (4)0.0011 (4)
O40.0373 (6)0.0288 (5)0.0297 (5)0.0091 (4)0.0128 (4)0.0015 (4)
C10.0199 (6)0.0212 (6)0.0182 (6)0.0025 (5)0.0061 (5)0.0027 (5)
C20.0186 (6)0.0206 (7)0.0219 (6)0.0018 (5)0.0063 (5)0.0031 (5)
C30.0262 (7)0.0216 (7)0.0257 (7)0.0006 (5)0.0097 (5)0.0014 (5)
C40.0233 (6)0.0263 (7)0.0235 (7)0.0022 (5)0.0106 (5)0.0014 (5)
C50.0207 (6)0.0249 (7)0.0223 (7)0.0002 (5)0.0062 (5)0.0033 (5)
C60.0229 (6)0.0195 (6)0.0227 (7)0.0008 (5)0.0073 (5)0.0003 (5)
C70.0212 (6)0.0160 (6)0.0264 (7)0.0010 (5)0.0112 (5)0.0015 (5)
C80.0234 (7)0.0182 (6)0.0258 (7)0.0022 (5)0.0080 (5)0.0008 (5)
C90.0191 (6)0.0240 (7)0.0339 (8)0.0015 (5)0.0078 (5)0.0014 (6)
C100.0242 (7)0.0210 (7)0.0345 (8)0.0005 (5)0.0154 (6)0.0015 (6)
C110.0251 (7)0.0183 (6)0.0282 (7)0.0007 (5)0.0125 (6)0.0006 (5)
C120.0192 (6)0.0180 (6)0.0269 (7)0.0003 (5)0.0083 (5)0.0005 (5)
C130.0368 (8)0.0190 (7)0.0533 (9)0.0036 (6)0.0228 (7)0.0007 (6)
C140.0249 (7)0.0302 (7)0.0316 (8)0.0035 (6)0.0128 (6)0.0002 (6)
C150.0287 (7)0.0448 (9)0.0351 (8)0.0069 (6)0.0006 (6)0.0019 (7)
C160.0282 (7)0.0281 (7)0.0314 (8)0.0065 (6)0.0138 (6)0.0010 (6)
Geometric parameters (Å, º) top
O1—C21.374 (1)C7—C121.388 (2)
O1—C131.426 (2)C8—C91.387 (2)
O2—C141.424 (2)C9—C101.388 (2)
O2—H1O20.89 (2)C9—H90.98
O3—C81.370 (1)C10—C111.383 (2)
O3—C151.431 (2)C10—H100.98
O4—C161.434 (2)C11—C121.398 (2)
O4—H1O40.94 (2)C11—C161.506 (2)
C1—C21.403 (2)C12—H120.98
C1—C61.392 (2)C13—H13C0.98
C1—C71.492 (2)C13—H13A0.98
C2—C31.384 (2)C13—H13B0.98
C3—C41.391 (2)C14—H14A0.98
C3—H30.98C14—H14B0.98
C4—C51.383 (2)C15—H15B0.98
C4—H40.98C15—H15C0.98
C5—C61.396 (2)C15—H15A0.98
C5—C141.502 (2)C16—H16A0.98
C6—H60.98C16—H16B0.98
C7—C81.407 (2)
C2—O1—C13117.17 (9)C9—C10—H10119.2
C14—O2—H1O2111 (1)C11—C10—H10119.2
C8—O3—C15117.5 (1)C10—C11—C12117.9 (1)
C16—O4—H1O4107 (1)C10—C11—C16121.2 (1)
C2—C1—C6117.9 (1)C12—C11—C16120.9 (1)
C2—C1—C7121.4 (1)C7—C12—C11122.2 (1)
C6—C1—C7120.7 (1)C7—C12—H12118.9
O1—C2—C1115.7 (1)C11—C12—H12118.9
O1—C2—C3123.2 (1)O1—C13—H13C109.5
C1—C2—C3121.1 (1)O1—C13—H13A109.5
C2—C3—C4119.4 (1)O1—C13—H13B109.5
C2—C3—H3120.3H13C—C13—H13A109.5
C4—C3—H3120.3H13C—C13—H13B109.5
C3—C4—C5121.2 (1)H13A—C13—H13B109.5
C3—C4—H4119.4O2—C14—C5108.0 (1)
C5—C4—H4119.4O2—C14—H14A109.8
C4—C5—C6118.5 (1)O2—C14—H14B109.8
C4—C5—C14120.6 (1)C5—C14—H14A109.8
C6—C5—C14120.9 (1)C5—C14—H14B109.8
C1—C6—C5121.9 (1)H14A—C14—H14B109.5
C1—C6—H6119.0O3—C15—H15B109.5
C5—C6—H6119.1O3—C15—H15C109.5
C1—C7—C8122.0 (1)O3—C15—H15A109.5
C1—C7—C12119.5 (1)H15B—C15—H15C109.5
C8—C7—C12118.5 (1)H15B—C15—H15A109.5
O3—C8—C7115.7 (1)H15C—C15—H15A109.5
O3—C8—C9124.3 (1)O4—C16—C11111.2 (1)
C7—C8—C9120.0 (1)O4—C16—H16A109.0
C8—C9—C10119.9 (1)O4—C16—H16B109.0
C8—C9—H9120.0C11—C16—H16A109.1
C10—C9—H9120.0C11—C16—H16B109.0
C9—C10—C11121.5 (1)H16A—C16—H16B109.5
O1—C2—C1—C6175.0 (1)C2—C3—C4—C51.7 (2)
O1—C2—C1—C71.6 (2)C3—C2—O1—C1318.3 (2)
O1—C2—C3—C4176.9 (1)C3—C2—C1—C63.4 (2)
O2—C14—C5—C496.1 (1)C3—C2—C1—C7180.0 (1)
O2—C14—C5—C680.3 (1)C3—C4—C5—C62.8 (2)
O3—C8—C7—C10.1 (2)C3—C4—C5—C14179.3 (1)
O3—C8—C7—C12179.4 (1)C5—C6—C1—C7178.9 (1)
O3—C8—C9—C10179.4 (1)C6—C1—C7—C8114.5 (1)
O4—C16—C11—C10137.3 (1)C6—C1—C7—C1264.9 (1)
O4—C16—C11—C1242.4 (2)C7—C8—O3—C15179.1 (1)
C1—C2—O1—C13160.2 (1)C7—C8—C9—C101.9 (2)
C1—C2—C3—C41.5 (2)C7—C12—C11—C102.1 (2)
C1—C6—C5—C40.8 (2)C7—C12—C11—C16177.6 (1)
C1—C6—C5—C14177.2 (1)C8—C7—C12—C111.4 (2)
C1—C7—C8—C9178.7 (1)C8—C9—C10—C111.1 (2)
C1—C7—C12—C11179.2 (1)C9—C8—O3—C150.3 (2)
C2—C1—C6—C52.3 (2)C9—C8—C7—C120.7 (2)
C2—C1—C7—C869.0 (2)C9—C10—C11—C120.8 (2)
C2—C1—C7—C12111.6 (1)C9—C10—C11—C16178.9 (1)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H1O2···O4i0.89 (2)1.92 (2)2.761 (1)157 (2)
O4—H1O4···O2ii0.94 (2)1.77 (2)2.699 (1)168 (2)
C10—H10···O1iii0.982.413.201 (1)137
C3—H3···O4iv0.982.523.490 (1)170
C12—H12···O2v0.982.673.380 (2)129
C15—H15C···O1vi0.982.693.574 (2)150
C4—H4···O2vii0.982.723.377 (2)125
C14—H14A···O1i0.982.763.637 (2)149
C13—H13C···O4iv0.982.763.557 (2)139
Symmetry codes: (i) x, y1/2, z+3/2; (ii) x, y1/2, z1/2; (iii) x+1, y1/2, 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.
Basic first- and second-level graph-set descriptors involving interactions designated a-i in order as given in Table 2. top
abcdefghi
aC(11)R44(8)C22(13)R42(16)R22(7)C22(16)C22(12)R22(12)R42(22)
bC(11)R44(26)C22(8)R42(14)C22(17)C21(12)R44(24)C22(11)
cC(8)R44(18)C22(12)C21(8)C22(15)C21(11)R44(16)
dC(9)R44(22)C22(13)C22(14)R44(28)R21(7)
eC(8)C22(14)C22(9)R22(9)R44(28)
fR22(16)C22(15)C21(11)C22(12)
gR22(10)C22(8)C22(17)
hC(7)R44(34)
iC(10)
 

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