Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100007022/fr1277sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100007022/fr1277Isup2.hkl |
CCDC reference: 150356
(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).
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.
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).
C22H26O4 | Z = 2 |
Mr = 354.45 | F(000) = 380 |
Triclinic, P1 | Dx = 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 |
Nonius KappaCCD diffractometer | 3340 reflections with I > 2.00σI |
Radiation source: X-ray tube | Rint = 0.024 |
Graphite monochromator | θmax = 27.5° |
ω scans with κ offsets | h = −11→11 |
22068 measured reflections | k = −13→13 |
4374 independent reflections | l = −14→14 |
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/[σ2cs + (0.035I)2] |
wR(F2) = 0.125 | (Δ/σ)max = 0.0003 |
S = 1.94 | Δρmax = 0.33 e Å−3 |
4374 reflections | Δρmin = −0.24 e Å−3 |
C22H26O4 | γ = 113.3672 (9)° |
Mr = 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)° |
Nonius KappaCCD diffractometer | 3340 reflections with I > 2.00σI |
22068 measured reflections | Rint = 0.024 |
4374 independent reflections |
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 | Δρmax = 0.33 e Å−3 |
4374 reflections | Δρmin = −0.24 e Å−3 |
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 |
x | y | z | Uiso*/Ueq | ||
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)* |
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) |
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···H3iv | 2.7105 | H10A···C7 | 2.501 (14) |
O4···H11Biv | 2.73 (2) | H11B···C11 | 0.98 (2) |
O4···C11iv | 3.511 (2) | H11B···C10 | 2.00 (2) |
C3···C7iv | 3.5757 (18) | H11B···O1 | 2.551 (19) |
C4···H10Aiv | 3.018 (15) | H11C···C11 | 1.02 (2) |
C7···H20Bi | 3.015 (19) | H11C···C10 | 2.06 (2) |
C11···H22Av | 2.95 (2) | H11C···O1 | 2.578 (19) |
C15···C15vi | 3.584 (3) | H11A···C11 | 1.002 (17) |
C15···C16vi | 3.5936 (17) | H11A···C10 | 2.073 (16) |
C16···H8Cvii | 3.045 (18) | H14···C14 | 0.9799 |
C19···H21Aviii | 2.952 (17) | H14···C15 | 2.0536 |
H3···H21Aiv | 2.4412 | H14···C13 | 2.0581 |
H8A···H20Aix | 2.55 (3) | H14···O3 | 2.4248 |
H8B···H19Ax | 2.61 (2) | H14···C18 | 2.6385 |
H9A···H15vi | 2.6634 | H15···C15 | 0.9800 |
H9C···H22Cxi | 2.56 (3) | H15···C16 | 2.0480 |
H10A···H10Aii | 2.63 (3) | H15···C14 | 2.0491 |
H11C···H14v | 2.6460 | H15···C19 | 2.6473 |
H11A···H22Av | 2.57 (3) | H19A···C19 | 0.971 (19) |
H14···H22Axii | 2.4711 | H19A···C16 | 2.042 (19) |
H19A···H21Aviii | 2.70 (2) | H19B···C19 | 0.923 (18) |
H19B···H21Aviii | 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. |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O4iv | 0.98 | 2.71 | 3.671 (2) | 167 |
C11—H11B···O4iv | 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 |
Mr | 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 > 2.00σI) reflections | 22068, 4374, 3340 |
Rint | 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 |
Δρmax, Δρmin (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).
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) |
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. |
a | b | c | |
a | R22(16) | R21(9) | C21(11) |
b | R22(22) | C21(14) | |
c | R22(10) |
Subscribe to Acta Crystallographica Section C: Structural Chemistry
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- Purchase subscription
- Reduced-price subscriptions
- If you have already subscribed, you may need to register
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.