C—H⋯O interactions in diethyl 5,5′,6,6′-tetra­methyl­bi­phenyl-2,2′-di­carboxyl­ate at 193 K

Gerkin, R.E.

doi:10.1107/S0108270100007022

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C—HO interactions in diethyl 5,5′,6,6′-tetramethylbiphenyl-2,2′-dicarboxylate at 193 K

R. E. Gerkin

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)°.

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Supporting information

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

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

	Fig. 1. Compound (I), showing the labeling scheme, with displacement ellipsoids at the 50% level.
	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

C₂₂H₂₆O₄	Z = 2
M_r = 354.45	F(000) = 380
Triclinic, P1	D_x = 1.227 Mg m⁻³
a = 8.9719 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.7632 (2) Å	Cell parameters from 22068 reflections
c = 10.8399 (2) Å	θ = 2.1–27.5°
α = 92.9965 (10)°	µ = 0.08 mm⁻¹
β = 90.1788 (10)°	T = 193 K
γ = 113.3672 (9)°	Cut slab, colorless
V = 959.28 (3) Å³	0.42 × 0.35 × 0.27 mm

Data collection top

Nonius KappaCCD diffractometer	3340 reflections with I > 2.00σ_I
Radiation source: X-ray tube	R_int = 0.024
Graphite monochromator	θ_max = 27.5°
ω scans with κ offsets	h = −11→11
22068 measured reflections	k = −13→13
4374 independent reflections	l = −14→14

Refinement top

Refinement on F²	323 parameters
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.050	Weighting scheme based on measured s.u.'s 1/[σ²_cs + (0.035I)²]
wR(F²) = 0.125	(Δ/σ)_max = 0.0003
S = 1.94	Δρ_max = 0.33 e Å⁻³
4374 reflections	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₂H₂₆O₄	γ = 113.3672 (9)°
M_r = 354.45	V = 959.28 (3) Å³
Triclinic, P1	Z = 2
a = 8.9719 (2) Å	Mo Kα radiation
b = 10.7632 (2) Å	µ = 0.08 mm⁻¹
c = 10.8399 (2) Å	T = 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 > 2.00σ_I
22068 measured reflections	R_int = 0.024
4374 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	323 parameters
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.94	Δρ_max = 0.33 e Å⁻³
4374 reflections	Δρ_min = −0.24 e Å⁻³

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

	x	y	z	U_iso*/U_eq
O1	0.79720 (10)	0.61284 (9)	0.39659 (8)	0.0355 (3)
O2	0.87546 (13)	0.62151 (12)	0.59323 (9)	0.0563 (4)
O3	0.74400 (11)	0.50811 (9)	0.88235 (9)	0.0413 (3)
O4	0.55019 (11)	0.56939 (10)	0.81172 (9)	0.0487 (3)
C1	0.67753 (14)	0.78257 (12)	0.65115 (11)	0.0282 (3)
C2	0.67073 (14)	0.70307 (12)	0.54234 (10)	0.0272 (3)
C3	0.54356 (15)	0.67372 (13)	0.45688 (11)	0.0314 (3)
C4	0.42528 (15)	0.72337 (13)	0.47810 (12)	0.0354 (4)
C5	0.42901 (15)	0.80203 (13)	0.58430 (12)	0.0347 (4)
C6	0.55532 (15)	0.83135 (13)	0.67192 (11)	0.0324 (4)
C7	0.79275 (15)	0.64372 (13)	0.51711 (11)	0.0307 (3)
C8	0.2972 (2)	0.8542 (2)	0.60402 (17)	0.0491 (5)
C9	0.5578 (2)	0.9140 (2)	0.78889 (16)	0.0536 (5)
C10	0.90212 (18)	0.54402 (16)	0.36057 (13)	0.0373 (4)
C11	0.8627 (2)	0.4947 (2)	0.22909 (15)	0.0535 (5)
C12	0.81781 (14)	0.82272 (12)	0.74310 (10)	0.0285 (3)
C13	0.82464 (14)	0.73406 (12)	0.83094 (11)	0.0293 (3)
C14	0.95694 (15)	0.77237 (13)	0.91210 (11)	0.0338 (4)
C15	1.08113 (16)	0.89923 (14)	0.90838 (12)	0.0370 (4)
C16	1.07725 (15)	0.98923 (13)	0.82362 (12)	0.0344 (4)
C17	0.94439 (15)	0.95155 (12)	0.73983 (11)	0.0312 (3)
C18	0.69047 (15)	0.59783 (13)	0.83866 (11)	0.0321 (4)
C19	1.2160 (2)	1.12663 (17)	0.82153 (17)	0.0476 (5)
C20	0.9400 (2)	1.05159 (16)	0.64938 (15)	0.0467 (5)
C21	0.62088 (19)	0.37402 (14)	0.89885 (16)	0.0460 (4)
C22	0.7050 (3)	0.28438 (18)	0.9217 (2)	0.0621 (6)
H3	0.5380	0.6176	0.3814	0.038*
H4	0.3369	0.7026	0.4168	0.043*
H8C	0.244 (2)	0.8306 (17)	0.6823 (17)	0.072 (6)*
H8A	0.220 (2)	0.8250 (17)	0.5368 (17)	0.072 (5)*
H8B	0.3437 (19)	0.9535 (18)	0.6122 (14)	0.058 (5)*
H9B	0.447 (3)	0.884 (2)	0.8229 (19)	0.103 (7)*
H9A	0.629 (3)	0.919 (2)	0.852 (2)	0.109 (8)*
H9C	0.565 (3)	1.007 (3)	0.765 (2)	0.122 (9)*
H10B	1.0119 (19)	0.6040 (14)	0.3742 (13)	0.043 (4)*
H10A	0.8839 (17)	0.4727 (15)	0.4156 (14)	0.047 (4)*
H11B	0.749 (3)	0.428 (2)	0.2254 (18)	0.087 (6)*
H11C	0.886 (2)	0.5759 (19)	0.1766 (18)	0.081 (6)*
H11A	0.932 (2)	0.4466 (16)	0.1984 (14)	0.056 (4)*
H14	0.9624	0.7093	0.9722	0.041*
H15	1.1735	0.9258	0.9669	0.045*
H19A	1.273 (2)	1.1312 (17)	0.7447 (18)	0.074 (6)*
H19B	1.284 (2)	1.1380 (16)	0.8888 (16)	0.065 (5)*
H19C	1.181 (2)	1.2007 (18)	0.8304 (16)	0.071 (6)*
H20A	0.852 (2)	1.0110 (18)	0.5876 (17)	0.076 (5)*
H20B	1.042 (2)	1.0925 (18)	0.6054 (17)	0.080 (6)*
H20C	0.915 (2)	1.122 (2)	0.6891 (19)	0.088 (6)*
H21B	0.5546 (19)	0.3758 (14)	0.9659 (15)	0.050 (4)*
H21A	0.545 (2)	0.3442 (16)	0.8229 (17)	0.070 (5)*
H22A	0.780 (3)	0.319 (2)	0.999 (2)	0.096 (7)*
H22B	0.779 (3)	0.280 (2)	0.852 (2)	0.112 (8)*
H22C	0.613 (2)	0.1901 (19)	0.9392 (15)	0.070 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0397 (5)	0.0438 (6)	0.0308 (5)	0.0252 (4)	0.0022 (4)	−0.0003 (4)
O2	0.0649 (7)	0.0871 (9)	0.0408 (6)	0.0586 (7)	−0.0188 (5)	−0.0199 (5)
O3	0.0336 (5)	0.0320 (5)	0.0554 (6)	0.0089 (4)	−0.0046 (4)	0.0111 (4)
O4	0.0277 (6)	0.0487 (6)	0.0649 (7)	0.0086 (5)	−0.0042 (5)	0.0169 (5)
C1	0.0286 (7)	0.0267 (7)	0.0296 (6)	0.0111 (5)	0.0004 (5)	0.0024 (5)
C2	0.0267 (7)	0.0258 (7)	0.0298 (6)	0.0109 (5)	0.0012 (5)	0.0032 (5)
C3	0.0316 (7)	0.0338 (7)	0.0299 (6)	0.0142 (6)	−0.0004 (5)	0.0019 (5)
C4	0.0308 (7)	0.0410 (8)	0.0369 (7)	0.0168 (6)	−0.0048 (5)	0.0041 (6)
C5	0.0312 (7)	0.0337 (7)	0.0435 (8)	0.0168 (6)	0.0025 (6)	0.0062 (6)
C6	0.0340 (7)	0.0302 (7)	0.0363 (7)	0.0165 (6)	0.0020 (6)	0.0006 (6)
C7	0.0290 (7)	0.0314 (7)	0.0318 (7)	0.0126 (6)	−0.0022 (5)	−0.0024 (5)
C8	0.0433 (9)	0.0576 (12)	0.0586 (11)	0.0338 (8)	−0.0048 (8)	−0.0037 (9)
C9	0.0530 (11)	0.0628 (12)	0.0532 (10)	0.0344 (9)	−0.0035 (8)	−0.0186 (9)
C10	0.0339 (8)	0.0422 (9)	0.0412 (8)	0.0218 (7)	0.0021 (6)	−0.0044 (7)
C11	0.0561 (11)	0.0720 (12)	0.0445 (9)	0.0395 (10)	0.0029 (8)	−0.0082 (9)
C12	0.0281 (7)	0.0309 (7)	0.0286 (6)	0.0144 (6)	0.0015 (5)	−0.0025 (5)
C13	0.0274 (7)	0.0313 (7)	0.0298 (6)	0.0125 (6)	0.0006 (5)	−0.0017 (5)
C14	0.0333 (7)	0.0383 (8)	0.0306 (7)	0.0155 (6)	−0.0025 (5)	0.0001 (6)
C15	0.0311 (7)	0.0408 (8)	0.0358 (7)	0.0119 (6)	−0.0060 (6)	−0.0069 (6)
C16	0.0313 (7)	0.0320 (7)	0.0368 (7)	0.0102 (6)	0.0032 (6)	−0.0068 (6)
C17	0.0332 (7)	0.0291 (7)	0.0316 (7)	0.0132 (6)	0.0046 (5)	−0.0015 (5)
C18	0.0305 (7)	0.0362 (8)	0.0300 (6)	0.0135 (6)	0.0003 (5)	0.0032 (5)
C19	0.0383 (9)	0.0375 (9)	0.0554 (10)	0.0036 (7)	−0.0010 (8)	−0.0047 (7)
C20	0.0527 (10)	0.0356 (9)	0.0480 (9)	0.0130 (8)	−0.0011 (8)	0.0066 (7)
C21	0.0419 (9)	0.0345 (8)	0.0540 (9)	0.0059 (7)	−0.0017 (8)	0.0121 (7)
C22	0.0704 (12)	0.0393 (10)	0.0750 (13)	0.0203 (9)	−0.0045 (11)	0.0025 (9)

Geometric parameters (Å, º) top

O1—C7	1.3357 (14)	C11—H11B	0.98 (2)
O1—C10	1.4534 (15)	C11—H11C	1.02 (2)
O2—C7	1.2025 (15)	C11—H11A	1.002 (17)
O3—C18	1.3422 (15)	C12—C13	1.4007 (17)
O3—C21	1.4487 (17)	C12—C17	1.4035 (17)
O4—C18	1.2024 (15)	C13—C14	1.3857 (17)
C1—C2	1.4070 (17)	C13—C18	1.4897 (18)
C1—C6	1.4051 (17)	C14—C15	1.3808 (18)
C1—C12	1.5100 (16)	C14—H14	0.98
C2—C3	1.3917 (17)	C15—C16	1.3797 (19)
C2—C7	1.4899 (17)	C15—H15	0.98
C3—C4	1.3795 (18)	C16—C17	1.4077 (18)
C3—H3	0.98	C16—C19	1.5102 (19)
C4—C5	1.3851 (18)	C17—C20	1.5052 (19)
C4—H4	0.98	C19—H19A	0.971 (19)
C5—C6	1.4015 (18)	C19—H19B	0.923 (18)
C5—C8	1.5085 (19)	C19—H19C	0.966 (19)
C6—C9	1.5051 (19)	C20—H20A	0.977 (19)
C8—H8C	0.970 (19)	C20—H20B	0.98 (2)
C8—H8A	0.951 (18)	C20—H20C	0.95 (2)
C8—H8B	0.979 (17)	C21—C22	1.470 (2)
C9—H9B	1.00 (2)	C21—H21B	0.945 (16)
C9—H9A	0.92 (3)	C21—H21A	1.019 (18)
C9—H9C	1.03 (3)	C22—H22A	1.03 (2)
C10—C11	1.485 (2)	C22—H22B	1.02 (3)
C10—H10B	0.945 (15)	C22—H22C	1.050 (19)
C10—H10A	0.959 (16)

O1···H20Bⁱ	2.918 (18)	H10B···O1	1.981 (15)
O1···C20ⁱ	3.5060 (18)	H10B···C11	2.048 (15)
O2···H10Aⁱⁱ	2.725 (15)	H10B···C7	2.658 (14)
O2···H10Bⁱⁱ	3.012 (14)	H10A···C10	0.959 (16)
O2···C10ⁱⁱ	3.2117 (17)	H10A···O1	1.971 (16)
O3···H11Aⁱⁱ	2.897 (17)	H10A···C11	2.064 (15)
O4···H21Bⁱⁱⁱ	2.711 (16)	H10A···O2	2.461 (14)
O4···H3^iv	2.7105	H10A···C7	2.501 (14)
O4···H11B^iv	2.73 (2)	H11B···C11	0.98 (2)
O4···C11^iv	3.511 (2)	H11B···C10	2.00 (2)
C3···C7^iv	3.5757 (18)	H11B···O1	2.551 (19)
C4···H10A^iv	3.018 (15)	H11C···C11	1.02 (2)
C7···H20Bⁱ	3.015 (19)	H11C···C10	2.06 (2)
C11···H22A^v	2.95 (2)	H11C···O1	2.578 (19)
C15···C15^vi	3.584 (3)	H11A···C11	1.002 (17)
C15···C16^vi	3.5936 (17)	H11A···C10	2.073 (16)
C16···H8C^vii	3.045 (18)	H14···C14	0.9799
C19···H21A^viii	2.952 (17)	H14···C15	2.0536
H3···H21A^iv	2.4412	H14···C13	2.0581
H8A···H20A^ix	2.55 (3)	H14···O3	2.4248
H8B···H19A^x	2.61 (2)	H14···C18	2.6385
H9A···H15^vi	2.6634	H15···C15	0.9800
H9C···H22C^xi	2.56 (3)	H15···C16	2.0480
H10A···H10Aⁱⁱ	2.63 (3)	H15···C14	2.0491
H11C···H14^v	2.6460	H15···C19	2.6473
H11A···H22A^v	2.57 (3)	H19A···C19	0.971 (19)
H14···H22A^xii	2.4711	H19A···C16	2.042 (19)
H19A···H21A^viii	2.70 (2)	H19B···C19	0.923 (18)
H19B···H21A^viii	2.64 (2)	H19B···C16	2.008 (17)
H20A···H20Bⁱ	2.67 (3)	H19B···C15	2.513 (16)
H3···C3	0.9800	H19C···C19	0.966 (19)
H3···C4	2.0522	H19C···C16	2.086 (18)
H3···C2	2.0633	H20A···C20	0.977 (19)
H3···O1	2.3518	H20A···C17	2.08 (2)
H3···C7	2.6253	H20A···C1	2.471 (18)
H4···C4	0.9799	H20A···C12	2.629 (19)
H4···C3	2.0466	H20B···C20	0.98 (2)
H4···C5	2.0517	H20B···C17	2.09 (2)
H4···C8	2.6509	H20C···C20	0.95 (2)
H8C···C8	0.970 (19)	H20C···C17	2.05 (2)
H8C···C5	2.087 (19)	H21B···C21	0.945 (16)
H8A···C8	0.951 (18)	H21B···O3	1.990 (16)
H8A···C5	2.050 (19)	H21B···C22	2.006 (16)
H8A···C4	2.551 (18)	H21B···C18	2.673 (15)
H8B···C8	0.979 (17)	H21A···C21	1.019 (18)
H8B···C5	2.067 (17)	H21A···O3	2.022 (17)
H9B···C9	1.00 (2)	H21A···C22	2.100 (18)
H9B···C6	2.07 (2)	H21A···O4	2.416 (16)
H9B···C8	2.66 (2)	H21A···C18	2.511 (16)
H9B···C5	2.67 (2)	H22A···C22	1.03 (2)
H9A···C9	0.92 (3)	H22A···C21	2.07 (2)
H9A···C6	2.10 (2)	H22A···O3	2.57 (2)
H9A···C12	2.57 (2)	H22B···C22	1.02 (3)
H9A···C1	2.69 (2)	H22B···C21	2.09 (2)
H9C···C9	1.03 (3)	H22B···O3	2.60 (2)
H9C···C6	2.07 (3)	H22C···C22	1.050 (19)
H10B···C10	0.945 (15)	H22C···C21	2.024 (18)

C7—O1—C10	116.83 (10)	H11C—C11—H11A	107.4 (14)
C18—O3—C21	115.79 (10)	C1—C12—C13	121.46 (11)
C2—C1—C6	119.35 (10)	C1—C12—C17	119.13 (11)
C2—C1—C12	121.45 (11)	C13—C12—C17	119.41 (11)
C6—C1—C12	119.13 (10)	C12—C13—C14	120.18 (11)
C1—C2—C3	119.78 (11)	C12—C13—C18	120.72 (10)
C1—C2—C7	122.00 (10)	C14—C13—C18	119.10 (11)
C3—C2—C7	118.18 (10)	C13—C14—C15	120.13 (12)
C2—C3—C4	120.18 (11)	C13—C14—H14	119.9
C2—C3—H3	119.9	C15—C14—H14	119.9
C4—C3—H3	119.9	C14—C15—C16	121.04 (12)
C3—C4—C5	121.29 (11)	C14—C15—H15	119.5
C3—C4—H4	119.4	C16—C15—H15	119.5
C5—C4—H4	119.3	C15—C16—C17	119.57 (12)
C4—C5—C6	119.25 (11)	C15—C16—C19	119.56 (13)
C4—C5—C8	119.63 (12)	C17—C16—C19	120.87 (13)
C6—C5—C8	121.12 (12)	C12—C17—C16	119.66 (12)
C1—C6—C5	120.15 (11)	C12—C17—C20	121.27 (12)
C1—C6—C9	120.36 (12)	C16—C17—C20	119.07 (12)
C5—C6—C9	119.48 (12)	O3—C18—O4	122.86 (12)
O1—C7—O2	122.64 (11)	O3—C18—C13	111.66 (10)
O1—C7—C2	111.33 (10)	O4—C18—C13	125.47 (12)
O2—C7—C2	126.00 (11)	C16—C19—H19A	108.8 (10)
C5—C8—H8C	112.9 (11)	C16—C19—H19B	108.8 (10)
C5—C8—H8A	110.8 (11)	C16—C19—H19C	113.0 (10)
C5—C8—H8B	110.6 (9)	H19A—C19—H19B	110.9 (15)
H8C—C8—H8A	111.2 (15)	H19A—C19—H19C	110.1 (15)
H8C—C8—H8B	102.1 (14)	H19B—C19—H19C	105.3 (14)
H8A—C8—H8B	108.9 (14)	C17—C20—H20A	112.4 (11)
C6—C9—H9B	110.2 (11)	C17—C20—H20B	112.8 (11)
C6—C9—H9A	118.4 (13)	C17—C20—H20C	111.3 (12)
C6—C9—H9C	107.8 (13)	H20A—C20—H20B	107.8 (15)
H9B—C9—H9A	108.5 (17)	H20A—C20—H20C	102.7 (16)
H9B—C9—H9C	96.1 (16)	H20B—C20—H20C	109.3 (16)
H9A—C9—H9C	113.6 (17)	O3—C21—C22	107.50 (14)
O1—C10—C11	107.50 (12)	O3—C21—H21B	110.7 (9)
O1—C10—H10B	109.5 (8)	O3—C21—H21A	108.8 (9)
O1—C10—H10A	107.8 (9)	C22—C21—H21B	110.4 (9)
C11—C10—H10B	112.9 (9)	C22—C21—H21A	113.8 (9)
C11—C10—H10A	113.4 (8)	H21B—C21—H21A	105.6 (13)
H10B—C10—H10A	105.5 (12)	C21—C22—H22A	110.7 (12)
C10—C11—H11B	106.8 (12)	C21—C22—H22B	113.1 (13)
C10—C11—H11C	108.9 (10)	C21—C22—H22C	105.7 (10)
C10—C11—H11A	111.4 (9)	H22A—C22—H22B	105.1 (17)
H11B—C11—H11C	115.0 (15)	H22A—C22—H22C	108.2 (15)
H11B—C11—H11A	107.4 (14)	H22B—C22—H22C	114.1 (16)

O1—C7—C2—C1	−159.11 (11)	C3—C4—C5—C8	−179.94 (14)
O1—C7—C2—C3	23.34 (16)	C4—C3—C2—C7	178.20 (11)
O2—C7—O1—C10	2.93 (18)	C4—C5—C6—C9	−178.54 (14)
O2—C7—C2—C1	22.8 (2)	C5—C6—C1—C12	176.25 (11)
O2—C7—C2—C3	−154.72 (14)	C6—C1—C2—C7	−177.53 (11)
O3—C18—C13—C12	151.71 (11)	C6—C1—C12—C13	101.54 (14)
O3—C18—C13—C14	−28.33 (16)	C6—C1—C12—C17	−78.80 (15)
O4—C18—O3—C21	−1.70 (18)	C7—O1—C10—C11	168.43 (13)
O4—C18—C13—C12	−29.45 (19)	C7—C2—C1—C12	5.66 (18)
O4—C18—C13—C14	150.50 (13)	C8—C5—C6—C9	1.2 (2)
C1—C2—C3—C4	0.59 (19)	C9—C6—C1—C12	−4.5 (2)
C1—C6—C5—C4	0.7 (2)	C12—C13—C14—C15	1.31 (19)
C1—C6—C5—C8	−179.48 (13)	C12—C17—C16—C15	−0.27 (18)
C1—C12—C13—C14	178.33 (11)	C12—C17—C16—C19	179.41 (12)
C1—C12—C13—C18	−1.72 (17)	C13—C12—C17—C16	0.81 (18)
C1—C12—C17—C16	−178.86 (10)	C13—C12—C17—C20	−178.31 (12)
C1—C12—C17—C20	2.02 (18)	C13—C14—C15—C16	−0.8 (2)
C2—C1—C6—C5	−0.64 (19)	C13—C18—O3—C21	177.16 (11)
C2—C1—C6—C9	178.63 (13)	C14—C13—C12—C17	−1.33 (18)
C2—C1—C12—C13	−81.64 (15)	C14—C15—C16—C17	0.2 (2)
C2—C1—C12—C17	98.02 (14)	C14—C15—C16—C19	−179.44 (13)
C2—C3—C4—C5	−0.5 (2)	C15—C14—C13—C18	−178.64 (11)
C2—C7—O1—C10	−175.21 (11)	C15—C16—C17—C20	178.87 (13)
C3—C2—C1—C6	−0.02 (19)	C17—C12—C13—C18	178.62 (10)
C3—C2—C1—C12	−176.83 (11)	C18—O3—C21—C22	168.42 (13)
C3—C4—C5—C6	−0.2 (2)	C19—C16—C17—C20	−1.45 (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, z−1; (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) x−1, y, z; (xi) x, y+1, z; (xii) −x+2, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O4^iv	0.98	2.71	3.671 (2)	167
C11—H11B···O4^iv	0.98 (2)	2.73 (2)	3.511 (2)	137 (2)
C21—H21B···O4ⁱⁱⁱ	0.94 (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 formula	C₂₂H₂₆O₄
M_r	354.45
Crystal system, space group	Triclinic, 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)
V (Å³)	959.28 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.42 × 0.35 × 0.27

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed (I > 2.00σ_I) reflections	22068, 4374, 3340
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.125, 1.94
No. of reflections	4374
No. of parameters	323
No. of restraints	?
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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—C7	1.3357 (14)	O3—C18	1.3422 (15)
O1—C10	1.4534 (15)	O3—C21	1.4487 (17)
O2—C7	1.2025 (15)	O4—C18	1.2024 (15)

C7—O1—C10	116.83 (10)	O1—C10—C11	107.50 (12)
C18—O3—C21	115.79 (10)	O3—C18—O4	122.86 (12)
O1—C7—O2	122.64 (11)	O3—C18—C13	111.66 (10)
O1—C7—C2	111.33 (10)	O4—C18—C13	125.47 (12)
O2—C7—C2	126.00 (11)	O3—C21—C22	107.50 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O4ⁱ	0.98	2.71	3.671 (2)	167
C11—H11B···O4ⁱ	0.98 (2)	2.73 (2)	3.511 (2)	137.0 (15)
C21—H21B···O4ⁱⁱ	0.94 (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

	a	b	c
a	R₂²(16)	R₂¹(9)	C₂¹(11)
b		R₂²(22)	C₂¹(14)
c			R₂²(10)

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C—HO interactions in diethyl 5,5′,6,6′-tetra­methyl­bi­phenyl-2,2′-di­carboxyl­ate at 193 K

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C—HO interactions in diethyl 5,5′,6,6′-tetramethylbiphenyl-2,2′-dicarboxylate at 193 K