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The title compound, C22H26O4, crystallized in the centrosymmetric space group P\overline 1 with one mol­ecule as the asymmetric unit. Three leading intermolecular C—H...O interactions have H...O distances of 2.71, 2.73 (2) and 2.71 (2) Å and C—H...O angles of 167, 137.0 (15) and 163.1 (12)°. These interactions form ring and chain patterns. The bi­phenyl twist angle is 79.95 (6)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100007022/fr1277sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100007022/fr1277Isup2.hkl
Contains datablock I

CCDC reference: 150356

Comment top

This report is one of a series on hydrogen bonding and C—H···O interactions in aromatic compounds. In this compound, conventional hydrogen bonds are of course absent, but significant C—H···O interactions were anticipated. (I) crystallized in the centrosymmetric space group P1 with one molecule as the asymmetric unit. The refined molecule and the labeling scheme are given in Fig. 1. Three leading intermolecular C—H···O interactions (Taylor & Kennard, 1982; Steiner & Desiraju, 1998) are present in this structure. The geometric parameters of these are given in Table 2. The results of basic first- and second-level graph-set analysis (Bernstein et al., 1995) involving these interactions, labeled a-c for this purpose in the order of their appearance in Table 2, are given in Table 3. The three first-level rings occur about centers of symmetry; the second-level ring does not, consistent with the involvement of each interaction only once. Both chains propagate along [001]. These three interactions link a central molecule directly to only two neighboring molecules as shown in the stereodiagram, Fig. 2. It is of interest that, while atoms O2 and O4 are chemically equivalent, only O4 is involved in these leading interactions. \sch

The phenyl rings are closely planar, the maximum deviation of a C atom from the best-fit plane being 0.0045 (13) Å for the C1—C6 ring and 0.0065 (12) Å for the C12—C17 ring, while the average deviations are 0.0029 (12) and 0.003 (2) Å, respectively. The dihedral angle between the best-fit planes of these rings, the biphenyl twist angle, is 79.95 (6)°. This value may be compared with that observed for the dimethyl ester of a similar 6,6'-substituted biphenyl-2, 2'-dicarboxylic acid, dimethyl 6,6'-dimethoxy-3,3',5,5'-tetramethylbiphenyl-2,2'-dicarboxylate [hereafter, (II)] (Dobson & Gerkin, 1999), 71.3 (1)°; the mean deviation of the ring-C atoms in (II) from these planes is 0.008 (4) Å. In (I), the torsion angles C2—C1—C12—C13 and C2—C1—C12—C17 measure −81.6 (2) and 98.0 (2)°, respectively. The dihedral angle between the C7—O1—O2 plane and that of the phenyl ring to which it is attached is 23.0 (2)°; the corresponding dihedral angle involving the C18—O3—O4 plane is 28.8 (2)°. These values contrast strongly with the corresponding value observed for (II), 62.3 (2)°, but this is not inconsistent with differences in the ester groups and adjacent substituents on the rings in the two molecules.

Selected bond distances and angles of (I) are given in Table 1. A l l distances and angles fall within normal limits. In (I), the several closest intermolecular approaches, excluding pairs of atoms involved in the tabulated C—H···O interactions, exceed (but by statistically insignificant amounts) the corresponding Bondi (1964) van der Waals radius sums.

Experimental top

(I) was obtained as a large, colorless slab from a sample in the chemical collection of Dr M. S. Newman. This was cut to provide the experimental sample. A synthesis is described by Newman & Lilje (1979).

Refinement top

Fourier difference methods were used to locate initial H atom positions and all H atoms were refined. The four ring-H atoms were then made canonical, with C—H = 0.98 Å and Uiso = 1.2 × Ueq of the attached C atom. The range of the 22 refined C—H distances is 0.92 (2)–1.05 (2) Å, and the mean value is 0.98 (4) Å.

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, 1995); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN and PLATON (Spek, 1990).

Figures top
[Figure 1] Fig. 1. Compound (I), showing the labeling scheme, with displacement ellipsoids at the 50% level.
[Figure 2] Fig. 2. Stereopacking diagram of (I) viewed almost along the a axis. The finer interatomic lines depict the tabulated interactions.
(I) top
Crystal data top
C22H26O4Z = 2
Mr = 354.45F(000) = 380
Triclinic, P1Dx = 1.227 Mg m3
a = 8.9719 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.7632 (2) ÅCell parameters from 22068 reflections
c = 10.8399 (2) Åθ = 2.1–27.5°
α = 92.9965 (10)°µ = 0.08 mm1
β = 90.1788 (10)°T = 193 K
γ = 113.3672 (9)°Cut slab, colorless
V = 959.28 (3) Å30.42 × 0.35 × 0.27 mm
Data collection top
Nonius KappaCCD
diffractometer
3340 reflections with I > 2.00σI
Radiation source: X-ray tubeRint = 0.024
Graphite monochromatorθmax = 27.5°
ω scans with κ offsetsh = 1111
22068 measured reflectionsk = 1313
4374 independent reflectionsl = 1414
Refinement top
Refinement on F2323 parameters
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.050Weighting scheme based on measured s.u.'s 1/[σ2cs + (0.035I)2]
wR(F2) = 0.125(Δ/σ)max = 0.0003
S = 1.94Δρmax = 0.33 e Å3
4374 reflectionsΔρmin = 0.24 e Å3
Crystal data top
C22H26O4γ = 113.3672 (9)°
Mr = 354.45V = 959.28 (3) Å3
Triclinic, P1Z = 2
a = 8.9719 (2) ÅMo Kα radiation
b = 10.7632 (2) ŵ = 0.08 mm1
c = 10.8399 (2) ÅT = 193 K
α = 92.9965 (10)°0.42 × 0.35 × 0.27 mm
β = 90.1788 (10)°
Data collection top
Nonius KappaCCD
diffractometer
3340 reflections with I > 2.00σI
22068 measured reflectionsRint = 0.024
4374 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.050323 parameters
wR(F2) = 0.125H atoms treated by a mixture of independent and constrained refinement
S = 1.94Δρmax = 0.33 e Å3
4374 reflectionsΔρmin = 0.24 e Å3
Special details top

Experimental. The Laue group assignment and the centrosymmetry indicated by the intensity statistics led to assignment of the space group as P-1 (No. 2); since refinement proceeded well, it was adopted. In the later stages of refinement the extinction coefficient was positive but not statistically significant, and was not included in the final model. The maximum peak in the final difference map occurs \sim 1.4 Å from C7 and C10, the maximum negative peak ~0.9 Å from C2.

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

————– Plane number 1 —————

Atoms Defining Plane Distance e.s.d. C1 (1) 0.0018 0.0012 C2 (1) 0.0021 0.0012 C3 (1) −0.0042 0.0013 C4 (1) 0.0016 0.0013 C5 (1) 0.0032 0.0013 C6 (1) −0.0045 0.0013

Mean deviation from plane is 0.0029 angstroms Chi-squared: 38.8

————– Plane number 2 —————

Atoms Defining Plane Distance e.s.d. C12 (1) 0.0045 0.0011 C13 (1) −0.0065 0.0012 C14 (1) 0.0047 0.0013 C15 (1) −0.0004 0.0013 C16 (1) −0.0009 0.0012 C17 (1) −0.0013 0.0012

Mean deviation from plane is 0.0031 angstroms Chi-squared: 62.5

Dihedral angles between least-squares planes plane plane angle 2 1 79.95

————– Plane number 3 —————

Atoms Defining Plane Distance e.s.d. O1 (1) 0.0000 O2 (1) 0.0000 C7 (1) 0.0000

Mean deviation from plane is 0.0000 angstroms Chi-squared: 0.0

Dihedral angles between least-squares planes plane plane angle 3 1 23.02 3 2 88.05

————– Plane number 4 —————

Atoms Defining Plane Distance e.s.d. O3 (1) 0.0000 O4 (1) 0.0000 C18 (1) 0.0000

Mean deviation from plane is 0.0000 angstroms Chi-squared: 0.0

Dihedral angles between least-squares planes plane plane angle 4 1 108.71 4 2 151.18 4 3 91.25

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.79720 (10)0.61284 (9)0.39659 (8)0.0355 (3)
O20.87546 (13)0.62151 (12)0.59323 (9)0.0563 (4)
O30.74400 (11)0.50811 (9)0.88235 (9)0.0413 (3)
O40.55019 (11)0.56939 (10)0.81172 (9)0.0487 (3)
C10.67753 (14)0.78257 (12)0.65115 (11)0.0282 (3)
C20.67073 (14)0.70307 (12)0.54234 (10)0.0272 (3)
C30.54356 (15)0.67372 (13)0.45688 (11)0.0314 (3)
C40.42528 (15)0.72337 (13)0.47810 (12)0.0354 (4)
C50.42901 (15)0.80203 (13)0.58430 (12)0.0347 (4)
C60.55532 (15)0.83135 (13)0.67192 (11)0.0324 (4)
C70.79275 (15)0.64372 (13)0.51711 (11)0.0307 (3)
C80.2972 (2)0.8542 (2)0.60402 (17)0.0491 (5)
C90.5578 (2)0.9140 (2)0.78889 (16)0.0536 (5)
C100.90212 (18)0.54402 (16)0.36057 (13)0.0373 (4)
C110.8627 (2)0.4947 (2)0.22909 (15)0.0535 (5)
C120.81781 (14)0.82272 (12)0.74310 (10)0.0285 (3)
C130.82464 (14)0.73406 (12)0.83094 (11)0.0293 (3)
C140.95694 (15)0.77237 (13)0.91210 (11)0.0338 (4)
C151.08113 (16)0.89923 (14)0.90838 (12)0.0370 (4)
C161.07725 (15)0.98923 (13)0.82362 (12)0.0344 (4)
C170.94439 (15)0.95155 (12)0.73983 (11)0.0312 (3)
C180.69047 (15)0.59783 (13)0.83866 (11)0.0321 (4)
C191.2160 (2)1.12663 (17)0.82153 (17)0.0476 (5)
C200.9400 (2)1.05159 (16)0.64938 (15)0.0467 (5)
C210.62088 (19)0.37402 (14)0.89885 (16)0.0460 (4)
C220.7050 (3)0.28438 (18)0.9217 (2)0.0621 (6)
H30.53800.61760.38140.038*
H40.33690.70260.41680.043*
H8C0.244 (2)0.8306 (17)0.6823 (17)0.072 (6)*
H8A0.220 (2)0.8250 (17)0.5368 (17)0.072 (5)*
H8B0.3437 (19)0.9535 (18)0.6122 (14)0.058 (5)*
H9B0.447 (3)0.884 (2)0.8229 (19)0.103 (7)*
H9A0.629 (3)0.919 (2)0.852 (2)0.109 (8)*
H9C0.565 (3)1.007 (3)0.765 (2)0.122 (9)*
H10B1.0119 (19)0.6040 (14)0.3742 (13)0.043 (4)*
H10A0.8839 (17)0.4727 (15)0.4156 (14)0.047 (4)*
H11B0.749 (3)0.428 (2)0.2254 (18)0.087 (6)*
H11C0.886 (2)0.5759 (19)0.1766 (18)0.081 (6)*
H11A0.932 (2)0.4466 (16)0.1984 (14)0.056 (4)*
H140.96240.70930.97220.041*
H151.17350.92580.96690.045*
H19A1.273 (2)1.1312 (17)0.7447 (18)0.074 (6)*
H19B1.284 (2)1.1380 (16)0.8888 (16)0.065 (5)*
H19C1.181 (2)1.2007 (18)0.8304 (16)0.071 (6)*
H20A0.852 (2)1.0110 (18)0.5876 (17)0.076 (5)*
H20B1.042 (2)1.0925 (18)0.6054 (17)0.080 (6)*
H20C0.915 (2)1.122 (2)0.6891 (19)0.088 (6)*
H21B0.5546 (19)0.3758 (14)0.9659 (15)0.050 (4)*
H21A0.545 (2)0.3442 (16)0.8229 (17)0.070 (5)*
H22A0.780 (3)0.319 (2)0.999 (2)0.096 (7)*
H22B0.779 (3)0.280 (2)0.852 (2)0.112 (8)*
H22C0.613 (2)0.1901 (19)0.9392 (15)0.070 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0397 (5)0.0438 (6)0.0308 (5)0.0252 (4)0.0022 (4)0.0003 (4)
O20.0649 (7)0.0871 (9)0.0408 (6)0.0586 (7)0.0188 (5)0.0199 (5)
O30.0336 (5)0.0320 (5)0.0554 (6)0.0089 (4)0.0046 (4)0.0111 (4)
O40.0277 (6)0.0487 (6)0.0649 (7)0.0086 (5)0.0042 (5)0.0169 (5)
C10.0286 (7)0.0267 (7)0.0296 (6)0.0111 (5)0.0004 (5)0.0024 (5)
C20.0267 (7)0.0258 (7)0.0298 (6)0.0109 (5)0.0012 (5)0.0032 (5)
C30.0316 (7)0.0338 (7)0.0299 (6)0.0142 (6)0.0004 (5)0.0019 (5)
C40.0308 (7)0.0410 (8)0.0369 (7)0.0168 (6)0.0048 (5)0.0041 (6)
C50.0312 (7)0.0337 (7)0.0435 (8)0.0168 (6)0.0025 (6)0.0062 (6)
C60.0340 (7)0.0302 (7)0.0363 (7)0.0165 (6)0.0020 (6)0.0006 (6)
C70.0290 (7)0.0314 (7)0.0318 (7)0.0126 (6)0.0022 (5)0.0024 (5)
C80.0433 (9)0.0576 (12)0.0586 (11)0.0338 (8)0.0048 (8)0.0037 (9)
C90.0530 (11)0.0628 (12)0.0532 (10)0.0344 (9)0.0035 (8)0.0186 (9)
C100.0339 (8)0.0422 (9)0.0412 (8)0.0218 (7)0.0021 (6)0.0044 (7)
C110.0561 (11)0.0720 (12)0.0445 (9)0.0395 (10)0.0029 (8)0.0082 (9)
C120.0281 (7)0.0309 (7)0.0286 (6)0.0144 (6)0.0015 (5)0.0025 (5)
C130.0274 (7)0.0313 (7)0.0298 (6)0.0125 (6)0.0006 (5)0.0017 (5)
C140.0333 (7)0.0383 (8)0.0306 (7)0.0155 (6)0.0025 (5)0.0001 (6)
C150.0311 (7)0.0408 (8)0.0358 (7)0.0119 (6)0.0060 (6)0.0069 (6)
C160.0313 (7)0.0320 (7)0.0368 (7)0.0102 (6)0.0032 (6)0.0068 (6)
C170.0332 (7)0.0291 (7)0.0316 (7)0.0132 (6)0.0046 (5)0.0015 (5)
C180.0305 (7)0.0362 (8)0.0300 (6)0.0135 (6)0.0003 (5)0.0032 (5)
C190.0383 (9)0.0375 (9)0.0554 (10)0.0036 (7)0.0010 (8)0.0047 (7)
C200.0527 (10)0.0356 (9)0.0480 (9)0.0130 (8)0.0011 (8)0.0066 (7)
C210.0419 (9)0.0345 (8)0.0540 (9)0.0059 (7)0.0017 (8)0.0121 (7)
C220.0704 (12)0.0393 (10)0.0750 (13)0.0203 (9)0.0045 (11)0.0025 (9)
Geometric parameters (Å, º) top
O1—C71.3357 (14)C11—H11B0.98 (2)
O1—C101.4534 (15)C11—H11C1.02 (2)
O2—C71.2025 (15)C11—H11A1.002 (17)
O3—C181.3422 (15)C12—C131.4007 (17)
O3—C211.4487 (17)C12—C171.4035 (17)
O4—C181.2024 (15)C13—C141.3857 (17)
C1—C21.4070 (17)C13—C181.4897 (18)
C1—C61.4051 (17)C14—C151.3808 (18)
C1—C121.5100 (16)C14—H140.98
C2—C31.3917 (17)C15—C161.3797 (19)
C2—C71.4899 (17)C15—H150.98
C3—C41.3795 (18)C16—C171.4077 (18)
C3—H30.98C16—C191.5102 (19)
C4—C51.3851 (18)C17—C201.5052 (19)
C4—H40.98C19—H19A0.971 (19)
C5—C61.4015 (18)C19—H19B0.923 (18)
C5—C81.5085 (19)C19—H19C0.966 (19)
C6—C91.5051 (19)C20—H20A0.977 (19)
C8—H8C0.970 (19)C20—H20B0.98 (2)
C8—H8A0.951 (18)C20—H20C0.95 (2)
C8—H8B0.979 (17)C21—C221.470 (2)
C9—H9B1.00 (2)C21—H21B0.945 (16)
C9—H9A0.92 (3)C21—H21A1.019 (18)
C9—H9C1.03 (3)C22—H22A1.03 (2)
C10—C111.485 (2)C22—H22B1.02 (3)
C10—H10B0.945 (15)C22—H22C1.050 (19)
C10—H10A0.959 (16)
O1···H20Bi2.918 (18)H10B···O11.981 (15)
O1···C20i3.5060 (18)H10B···C112.048 (15)
O2···H10Aii2.725 (15)H10B···C72.658 (14)
O2···H10Bii3.012 (14)H10A···C100.959 (16)
O2···C10ii3.2117 (17)H10A···O11.971 (16)
O3···H11Aii2.897 (17)H10A···C112.064 (15)
O4···H21Biii2.711 (16)H10A···O22.461 (14)
O4···H3iv2.7105H10A···C72.501 (14)
O4···H11Biv2.73 (2)H11B···C110.98 (2)
O4···C11iv3.511 (2)H11B···C102.00 (2)
C3···C7iv3.5757 (18)H11B···O12.551 (19)
C4···H10Aiv3.018 (15)H11C···C111.02 (2)
C7···H20Bi3.015 (19)H11C···C102.06 (2)
C11···H22Av2.95 (2)H11C···O12.578 (19)
C15···C15vi3.584 (3)H11A···C111.002 (17)
C15···C16vi3.5936 (17)H11A···C102.073 (16)
C16···H8Cvii3.045 (18)H14···C140.9799
C19···H21Aviii2.952 (17)H14···C152.0536
H3···H21Aiv2.4412H14···C132.0581
H8A···H20Aix2.55 (3)H14···O32.4248
H8B···H19Ax2.61 (2)H14···C182.6385
H9A···H15vi2.6634H15···C150.9800
H9C···H22Cxi2.56 (3)H15···C162.0480
H10A···H10Aii2.63 (3)H15···C142.0491
H11C···H14v2.6460H15···C192.6473
H11A···H22Av2.57 (3)H19A···C190.971 (19)
H14···H22Axii2.4711H19A···C162.042 (19)
H19A···H21Aviii2.70 (2)H19B···C190.923 (18)
H19B···H21Aviii2.64 (2)H19B···C162.008 (17)
H20A···H20Bi2.67 (3)H19B···C152.513 (16)
H3···C30.9800H19C···C190.966 (19)
H3···C42.0522H19C···C162.086 (18)
H3···C22.0633H20A···C200.977 (19)
H3···O12.3518H20A···C172.08 (2)
H3···C72.6253H20A···C12.471 (18)
H4···C40.9799H20A···C122.629 (19)
H4···C32.0466H20B···C200.98 (2)
H4···C52.0517H20B···C172.09 (2)
H4···C82.6509H20C···C200.95 (2)
H8C···C80.970 (19)H20C···C172.05 (2)
H8C···C52.087 (19)H21B···C210.945 (16)
H8A···C80.951 (18)H21B···O31.990 (16)
H8A···C52.050 (19)H21B···C222.006 (16)
H8A···C42.551 (18)H21B···C182.673 (15)
H8B···C80.979 (17)H21A···C211.019 (18)
H8B···C52.067 (17)H21A···O32.022 (17)
H9B···C91.00 (2)H21A···C222.100 (18)
H9B···C62.07 (2)H21A···O42.416 (16)
H9B···C82.66 (2)H21A···C182.511 (16)
H9B···C52.67 (2)H22A···C221.03 (2)
H9A···C90.92 (3)H22A···C212.07 (2)
H9A···C62.10 (2)H22A···O32.57 (2)
H9A···C122.57 (2)H22B···C221.02 (3)
H9A···C12.69 (2)H22B···C212.09 (2)
H9C···C91.03 (3)H22B···O32.60 (2)
H9C···C62.07 (3)H22C···C221.050 (19)
H10B···C100.945 (15)H22C···C212.024 (18)
C7—O1—C10116.83 (10)H11C—C11—H11A107.4 (14)
C18—O3—C21115.79 (10)C1—C12—C13121.46 (11)
C2—C1—C6119.35 (10)C1—C12—C17119.13 (11)
C2—C1—C12121.45 (11)C13—C12—C17119.41 (11)
C6—C1—C12119.13 (10)C12—C13—C14120.18 (11)
C1—C2—C3119.78 (11)C12—C13—C18120.72 (10)
C1—C2—C7122.00 (10)C14—C13—C18119.10 (11)
C3—C2—C7118.18 (10)C13—C14—C15120.13 (12)
C2—C3—C4120.18 (11)C13—C14—H14119.9
C2—C3—H3119.9C15—C14—H14119.9
C4—C3—H3119.9C14—C15—C16121.04 (12)
C3—C4—C5121.29 (11)C14—C15—H15119.5
C3—C4—H4119.4C16—C15—H15119.5
C5—C4—H4119.3C15—C16—C17119.57 (12)
C4—C5—C6119.25 (11)C15—C16—C19119.56 (13)
C4—C5—C8119.63 (12)C17—C16—C19120.87 (13)
C6—C5—C8121.12 (12)C12—C17—C16119.66 (12)
C1—C6—C5120.15 (11)C12—C17—C20121.27 (12)
C1—C6—C9120.36 (12)C16—C17—C20119.07 (12)
C5—C6—C9119.48 (12)O3—C18—O4122.86 (12)
O1—C7—O2122.64 (11)O3—C18—C13111.66 (10)
O1—C7—C2111.33 (10)O4—C18—C13125.47 (12)
O2—C7—C2126.00 (11)C16—C19—H19A108.8 (10)
C5—C8—H8C112.9 (11)C16—C19—H19B108.8 (10)
C5—C8—H8A110.8 (11)C16—C19—H19C113.0 (10)
C5—C8—H8B110.6 (9)H19A—C19—H19B110.9 (15)
H8C—C8—H8A111.2 (15)H19A—C19—H19C110.1 (15)
H8C—C8—H8B102.1 (14)H19B—C19—H19C105.3 (14)
H8A—C8—H8B108.9 (14)C17—C20—H20A112.4 (11)
C6—C9—H9B110.2 (11)C17—C20—H20B112.8 (11)
C6—C9—H9A118.4 (13)C17—C20—H20C111.3 (12)
C6—C9—H9C107.8 (13)H20A—C20—H20B107.8 (15)
H9B—C9—H9A108.5 (17)H20A—C20—H20C102.7 (16)
H9B—C9—H9C96.1 (16)H20B—C20—H20C109.3 (16)
H9A—C9—H9C113.6 (17)O3—C21—C22107.50 (14)
O1—C10—C11107.50 (12)O3—C21—H21B110.7 (9)
O1—C10—H10B109.5 (8)O3—C21—H21A108.8 (9)
O1—C10—H10A107.8 (9)C22—C21—H21B110.4 (9)
C11—C10—H10B112.9 (9)C22—C21—H21A113.8 (9)
C11—C10—H10A113.4 (8)H21B—C21—H21A105.6 (13)
H10B—C10—H10A105.5 (12)C21—C22—H22A110.7 (12)
C10—C11—H11B106.8 (12)C21—C22—H22B113.1 (13)
C10—C11—H11C108.9 (10)C21—C22—H22C105.7 (10)
C10—C11—H11A111.4 (9)H22A—C22—H22B105.1 (17)
H11B—C11—H11C115.0 (15)H22A—C22—H22C108.2 (15)
H11B—C11—H11A107.4 (14)H22B—C22—H22C114.1 (16)
O1—C7—C2—C1159.11 (11)C3—C4—C5—C8179.94 (14)
O1—C7—C2—C323.34 (16)C4—C3—C2—C7178.20 (11)
O2—C7—O1—C102.93 (18)C4—C5—C6—C9178.54 (14)
O2—C7—C2—C122.8 (2)C5—C6—C1—C12176.25 (11)
O2—C7—C2—C3154.72 (14)C6—C1—C2—C7177.53 (11)
O3—C18—C13—C12151.71 (11)C6—C1—C12—C13101.54 (14)
O3—C18—C13—C1428.33 (16)C6—C1—C12—C1778.80 (15)
O4—C18—O3—C211.70 (18)C7—O1—C10—C11168.43 (13)
O4—C18—C13—C1229.45 (19)C7—C2—C1—C125.66 (18)
O4—C18—C13—C14150.50 (13)C8—C5—C6—C91.2 (2)
C1—C2—C3—C40.59 (19)C9—C6—C1—C124.5 (2)
C1—C6—C5—C40.7 (2)C12—C13—C14—C151.31 (19)
C1—C6—C5—C8179.48 (13)C12—C17—C16—C150.27 (18)
C1—C12—C13—C14178.33 (11)C12—C17—C16—C19179.41 (12)
C1—C12—C13—C181.72 (17)C13—C12—C17—C160.81 (18)
C1—C12—C17—C16178.86 (10)C13—C12—C17—C20178.31 (12)
C1—C12—C17—C202.02 (18)C13—C14—C15—C160.8 (2)
C2—C1—C6—C50.64 (19)C13—C18—O3—C21177.16 (11)
C2—C1—C6—C9178.63 (13)C14—C13—C12—C171.33 (18)
C2—C1—C12—C1381.64 (15)C14—C15—C16—C170.2 (2)
C2—C1—C12—C1798.02 (14)C14—C15—C16—C19179.44 (13)
C2—C3—C4—C50.5 (2)C15—C14—C13—C18178.64 (11)
C2—C7—O1—C10175.21 (11)C15—C16—C17—C20178.87 (13)
C3—C2—C1—C60.02 (19)C17—C12—C13—C18178.62 (10)
C3—C2—C1—C12176.83 (11)C18—O3—C21—C22168.42 (13)
C3—C4—C5—C60.2 (2)C19—C16—C17—C201.45 (19)
Symmetry codes: (i) x+2, y+2, z+1; (ii) x+2, y+1, z+1; (iii) x+1, y+1, z+2; (iv) x+1, y+1, z+1; (v) x, y, z1; (vi) x+2, y+2, z+2; (vii) x+1, y, z; (viii) x+1, y+1, z; (ix) x+1, y+2, z+1; (x) x1, y, z; (xi) x, y+1, z; (xii) x+2, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O4iv0.982.713.671 (2)167
C11—H11B···O4iv0.98 (2)2.73 (2)3.511 (2)137 (2)
C21—H21B···O4iii0.94 (2)2.71 (2)3.625 (2)163 (1)
Symmetry codes: (iii) x+1, y+1, z+2; (iv) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC22H26O4
Mr354.45
Crystal system, space groupTriclinic, P1
Temperature (K)193
a, b, c (Å)8.9719 (2), 10.7632 (2), 10.8399 (2)
α, β, γ (°)92.9965 (10), 90.1788 (10), 113.3672 (9)
V3)959.28 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.42 × 0.35 × 0.27
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed (I > 2.00σI) reflections
22068, 4374, 3340
Rint0.024
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.125, 1.94
No. of reflections4374
No. of parameters323
No. of restraints?
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.33, 0.24

Computer programs: COLLECT (Nonius, 1999), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXS86 (Sheldrick, 1990), TEXSAN (Molecular Structure Corporation, 1995), ORTEPII (Johnson, 1976), TEXSAN and PLATON (Spek, 1990).

Selected geometric parameters (Å, º) top
O1—C71.3357 (14)O3—C181.3422 (15)
O1—C101.4534 (15)O3—C211.4487 (17)
O2—C71.2025 (15)O4—C181.2024 (15)
C7—O1—C10116.83 (10)O1—C10—C11107.50 (12)
C18—O3—C21115.79 (10)O3—C18—O4122.86 (12)
O1—C7—O2122.64 (11)O3—C18—C13111.66 (10)
O1—C7—C2111.33 (10)O4—C18—C13125.47 (12)
O2—C7—C2126.00 (11)O3—C21—C22107.50 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O4i0.982.713.671 (2)167
C11—H11B···O4i0.98 (2)2.73 (2)3.511 (2)137.0 (15)
C21—H21B···O4ii0.94 (2)2.71 (2)3.625 (2)163.1 (12)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+1, z+2.
Basic first- and second-level graph set descriptors involving interactions designated a-c in order as given in Table 2. top
abc
aR22(16)R21(9)C21(11)
bR22(22)C21(14)
cR22(10)
 

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