Tetra­methyl bi­phenyl-3,5,3′,5′-tetra­carboxyl­ate benzene sesquisolvate

Coles, S.J.; Gale, P.A.; Hursthouse, M.B.; Warriner, C.N.

doi:10.1107/S1600536802010978

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Tetramethyl biphenyl-3,5,3',5'-tetracarboxylate benzene sesquisolvate

S. J. Coles, P. A. Gale, M. B. Hursthouse and C. N. Warriner

The title structure, C₂₀H₁₈O₈·1.5C₆H₆, is a tetrasubstituted biphenyl which has a pseudo-inversion centre between the two halves. The benzene solvent molecules lie in special positions, one with twofold rotation symmetry and two with inversion symmetry. The tetramethyl ester molecule is twisted and forms a supramolecular assembly of stacked sheets.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802010978/om6092sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536802010978/om6092Isup2.hkl Contains datablock I

CCDC reference: 193760

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.005 Å
R factor = 0.053
wR factor = 0.148
Data-to-parameter ratio = 8.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



CELLV_02  Alert B The supplied cell volume s.u. differs from that
          calculated from the cell parameter s.u.'s by > 4
          Calculated cell volume su =      23.98
          Cell volume su given      =      16.00

RINTA_01  Alert B The value of Rint is greater than 0.15
          Rint given   0.167

THETM_01  Alert B The value of sine(theta_max)/wavelength is less than 0.575
          Calculated sin(theta_max)/wavelength =    0.5635


 Alert Level C:



REFNR_01  Alert C Ratio of reflections to parameters is < 10 for a
          centrosymmetric structure
          sine(theta)/lambda                0.5635
          Proportion of unique data used    1.0000
          Ratio reflections to parameters   8.2398


 0 Alert Level A = Potentially serious problem

 3 Alert Level B = Potential problem

 1 Alert Level C = Please check

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990).

(I) top

Crystal data top

C₂₀H₁₈O₈·1.5C₆H₆	F(000) = 2120
M_r = 503.51	D_x = 1.362 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 37.557 (7) Å	Cell parameters from 16139 reflections
b = 7.0816 (14) Å	θ = 5.1–23.2°
c = 22.498 (4) Å	µ = 0.10 mm⁻¹
β = 124.86 (3)°	T = 150 K
V = 4909.9 (16) Å³	Needle, colourless
Z = 8	0.48 × 0.07 × 0.01 mm

Data collection top

Nonius KappaCCD area-detector diffractometer	2251 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.167
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	θ_max = 23.6°, θ_min = 3.0°
T_min = 0.954, T_max = 0.999	h = −42→42
18113 measured reflections	k = −7→7
3642 independent reflections	l = −25→25

Refinement top

Refinement on F²	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0627P)²] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.053	(Δ/σ)_max = 0.001
wR(F²) = 0.148	Δρ_max = 0.24 e Å⁻³
S = 1.01	Δρ_min = −0.26 e Å⁻³
3642 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
442 parameters	Extinction coefficient: 0.0019 (3)
0 restraints

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.33850 (13)	0.8414 (5)	0.1315 (2)	0.0424 (9)
C2	0.34335 (10)	0.9533 (4)	0.23485 (15)	0.0314 (7)
C3	0.31925 (9)	0.9927 (4)	0.26761 (14)	0.0268 (7)
C4	0.34302 (10)	1.0389 (4)	0.34103 (15)	0.0277 (7)
C5	0.32153 (9)	1.0802 (4)	0.37270 (14)	0.0267 (7)
C6	0.34488 (10)	1.1377 (4)	0.45050 (14)	0.0292 (7)
C7	0.41302 (13)	1.1704 (6)	0.56249 (16)	0.0443 (9)
C8	0.27641 (10)	1.0754 (4)	0.33196 (15)	0.0280 (7)
C9	0.25190 (9)	1.0276 (4)	0.25802 (14)	0.0265 (7)
C10	0.27431 (9)	0.9894 (4)	0.22715 (15)	0.0284 (7)
C11	0.20367 (9)	1.0244 (4)	0.21519 (14)	0.0271 (7)
C12	0.18215 (9)	0.9779 (4)	0.24687 (15)	0.0285 (7)
C13	0.13682 (9)	0.9779 (4)	0.20660 (14)	0.0285 (7)
C14	0.11293 (10)	0.9323 (4)	0.23935 (15)	0.0329 (7)
C15	0.11867 (13)	0.8514 (6)	0.34632 (19)	0.0466 (9)
C16	0.11261 (11)	1.0236 (4)	0.13341 (15)	0.0301 (7)
C17	0.13372 (9)	1.0696 (4)	0.10097 (14)	0.0284 (7)
C18	0.10931 (10)	1.1270 (4)	0.02343 (15)	0.0316 (7)
C19	0.03967 (12)	1.1579 (6)	−0.08656 (17)	0.0462 (9)
C20	0.17860 (10)	1.0708 (4)	0.14144 (15)	0.0286 (7)
C41	0.02442 (13)	0.4903 (8)	0.2332 (2)	0.0680 (14)
C42	0.02429 (17)	0.2999 (9)	0.2335 (2)	0.0851 (18)
C43	0	0.2056 (9)	0.25	0.101 (3)
H43	0	0.0714	0.25	0.122*
C46	0	0.5856 (8)	0.25	0.0647 (19)
C47	0.02532 (13)	0.4071 (6)	0.06563 (19)	0.0542 (10)
C48	−0.00793 (13)	0.3137 (5)	0.0049 (2)	0.0559 (10)
C49	0.03294 (12)	0.5926 (6)	0.0603 (2)	0.0561 (10)
C53	0.22795 (12)	0.2878 (5)	0.03085 (17)	0.0451 (9)
C54	0.22907 (11)	0.1050 (5)	0.00972 (17)	0.0434 (9)
C55	0.24901 (11)	0.4311 (5)	0.02140 (17)	0.0435 (8)
O1	0.31812 (7)	0.8772 (3)	0.16853 (10)	0.0374 (6)
O2	0.38157 (7)	0.9838 (3)	0.26444 (11)	0.0467 (6)
O3	0.32699 (7)	1.1884 (3)	0.47805 (10)	0.0414 (6)
O4	0.38786 (7)	1.1263 (3)	0.48526 (10)	0.0375 (6)
O5	0.07384 (7)	0.9327 (3)	0.20671 (11)	0.0408 (6)
O6	0.13971 (7)	0.8915 (3)	0.31015 (10)	0.0392 (6)
O7	0.12573 (7)	1.1907 (3)	−0.00503 (11)	0.0456 (6)
O8	0.06665 (7)	1.0959 (3)	−0.01136 (10)	0.0388 (6)
H1A	0.3409 (12)	0.958 (5)	0.110 (2)	0.072 (12)*
H1B	0.3187 (12)	0.754 (5)	0.092 (2)	0.070 (11)*
H1C	0.3676 (14)	0.785 (5)	0.163 (2)	0.078 (13)*
H4	0.3741 (9)	1.035 (3)	0.3687 (14)	0.025 (7)*
H7A	0.4026 (13)	1.305 (6)	0.570 (2)	0.090 (13)*
H7B	0.4453 (14)	1.175 (5)	0.578 (2)	0.075 (12)*
H7C	0.4067 (11)	1.072 (5)	0.5851 (18)	0.060 (11)*
H8	0.2611 (9)	1.100 (4)	0.3563 (15)	0.034 (8)*
H10	0.2582 (10)	0.964 (4)	0.1761 (16)	0.042 (8)*
H12	0.1979 (8)	0.947 (3)	0.2965 (14)	0.021 (7)*
H15A	0.0976 (13)	0.960 (5)	0.338 (2)	0.076 (13)*
H15B	0.1444 (12)	0.827 (5)	0.401 (2)	0.067 (11)*
H15C	0.0996 (12)	0.733 (5)	0.3227 (18)	0.066 (11)*
H16	0.0832 (10)	1.028 (4)	0.1094 (15)	0.031 (8)*
H19A	0.0389 (14)	1.308 (7)	−0.085 (2)	0.102 (15)*
H19B	0.0093 (13)	1.114 (5)	−0.1077 (19)	0.064 (11)*
H19C	0.0507 (11)	1.107 (5)	−0.1126 (18)	0.056 (10)*
H20	0.1941 (9)	1.102 (3)	0.1193 (14)	0.025 (7)*
H41	0.0410 (16)	0.552 (6)	0.220 (2)	0.109 (17)*
H42	0.0403 (17)	0.233 (7)	0.216 (3)	0.127 (18)*
H46	0	0.715 (8)	0.25	0.066 (16)*
H47	0.0443 (13)	0.337 (5)	0.115 (2)	0.074 (11)*
H48	−0.0135 (13)	0.185 (6)	0.012 (2)	0.081 (13)*
H49	0.0565 (15)	0.659 (6)	0.106 (2)	0.102 (15)*
H53	0.2108 (10)	0.315 (4)	0.0520 (16)	0.048 (9)*
H54	0.2150 (11)	0.010 (5)	0.0172 (19)	0.062 (11)*
H55	0.2478 (11)	0.561 (5)	0.0362 (18)	0.059 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.046 (3)	0.055 (2)	0.034 (2)	−0.0003 (19)	0.027 (2)	−0.0040 (17)
C2	0.029 (2)	0.0355 (17)	0.0253 (16)	0.0013 (14)	0.0134 (15)	0.0049 (13)
C3	0.0276 (18)	0.0272 (15)	0.0247 (16)	−0.0021 (13)	0.0143 (14)	−0.0001 (11)
C4	0.0216 (18)	0.0313 (16)	0.0239 (16)	0.0012 (13)	0.0092 (14)	0.0037 (12)
C5	0.0291 (18)	0.0243 (14)	0.0247 (15)	−0.0017 (12)	0.0141 (14)	0.0012 (11)
C6	0.0270 (19)	0.0334 (16)	0.0240 (16)	−0.0040 (13)	0.0127 (15)	0.0023 (12)
C7	0.038 (2)	0.063 (2)	0.0202 (17)	−0.0088 (18)	0.0096 (17)	−0.0044 (15)
C8	0.0296 (19)	0.0290 (15)	0.0267 (16)	0.0003 (13)	0.0168 (15)	0.0016 (12)
C9	0.0257 (17)	0.0276 (16)	0.0223 (15)	−0.0012 (12)	0.0113 (14)	−0.0001 (11)
C10	0.0298 (19)	0.0263 (15)	0.0228 (17)	−0.0025 (13)	0.0113 (15)	−0.0002 (12)
C11	0.0261 (18)	0.0285 (16)	0.0242 (16)	−0.0009 (12)	0.0130 (14)	−0.0034 (11)
C12	0.0287 (19)	0.0287 (16)	0.0221 (16)	−0.0008 (13)	0.0109 (15)	−0.0050 (12)
C13	0.0265 (18)	0.0317 (16)	0.0241 (16)	0.0012 (13)	0.0125 (14)	−0.0029 (12)
C14	0.031 (2)	0.0361 (17)	0.0277 (17)	−0.0011 (14)	0.0144 (16)	−0.0029 (13)
C15	0.045 (2)	0.067 (3)	0.034 (2)	−0.007 (2)	0.0263 (19)	0.0011 (18)
C16	0.0264 (19)	0.0343 (17)	0.0264 (17)	0.0001 (14)	0.0131 (15)	−0.0038 (12)
C17	0.0273 (18)	0.0298 (16)	0.0243 (15)	0.0002 (13)	0.0126 (14)	−0.0006 (12)
C18	0.028 (2)	0.0350 (17)	0.0284 (17)	0.0039 (13)	0.0144 (16)	0.0010 (13)
C19	0.031 (2)	0.076 (3)	0.0215 (18)	0.0076 (19)	0.0087 (17)	0.0073 (16)
C20	0.0290 (19)	0.0306 (16)	0.0269 (16)	−0.0013 (13)	0.0163 (15)	−0.0019 (12)
C41	0.040 (3)	0.129 (5)	0.029 (2)	−0.024 (3)	0.0165 (19)	−0.008 (2)
C42	0.077 (4)	0.121 (5)	0.029 (2)	0.060 (4)	0.013 (2)	0.000 (3)
C43	0.159 (9)	0.047 (4)	0.024 (3)	0	0.009 (4)	0
C46	0.089 (5)	0.043 (3)	0.027 (3)	0	0.012 (3)	0
C47	0.050 (3)	0.068 (3)	0.041 (2)	0.014 (2)	0.023 (2)	0.0006 (19)
C48	0.057 (3)	0.051 (2)	0.067 (3)	−0.005 (2)	0.040 (2)	−0.005 (2)
C49	0.036 (2)	0.073 (3)	0.048 (2)	−0.002 (2)	0.017 (2)	−0.020 (2)
C53	0.047 (2)	0.052 (2)	0.041 (2)	0.0005 (17)	0.0278 (19)	−0.0033 (15)
C54	0.040 (2)	0.047 (2)	0.0405 (19)	−0.0049 (17)	0.0212 (18)	−0.0005 (15)
C55	0.042 (2)	0.043 (2)	0.042 (2)	−0.0024 (16)	0.0220 (18)	−0.0059 (16)
O1	0.0370 (14)	0.0502 (13)	0.0262 (11)	−0.0028 (10)	0.0187 (11)	−0.0059 (9)
O2	0.0314 (15)	0.0762 (16)	0.0306 (13)	−0.0052 (12)	0.0165 (12)	−0.0072 (11)
O3	0.0357 (14)	0.0602 (15)	0.0290 (12)	−0.0026 (11)	0.0190 (12)	−0.0071 (10)
O4	0.0289 (14)	0.0532 (13)	0.0220 (11)	−0.0011 (10)	0.0096 (10)	−0.0021 (9)
O5	0.0312 (15)	0.0561 (14)	0.0349 (12)	−0.0014 (10)	0.0187 (12)	−0.0008 (10)
O6	0.0330 (14)	0.0603 (14)	0.0255 (11)	−0.0073 (10)	0.0174 (11)	−0.0015 (9)
O7	0.0363 (15)	0.0685 (15)	0.0307 (12)	0.0021 (11)	0.0185 (12)	0.0089 (10)
O8	0.0280 (13)	0.0570 (14)	0.0219 (11)	0.0028 (10)	0.0086 (10)	0.0036 (9)

Geometric parameters (Å, º) top

C1—O1	1.440 (4)	C15—H15C	1.03 (4)
C1—H1A	0.98 (4)	C16—C17	1.389 (4)
C1—H1B	0.99 (4)	C16—H16	0.91 (3)
C1—H1C	0.99 (4)	C17—C20	1.384 (4)
C2—O2	1.207 (3)	C17—C18	1.490 (4)
C2—O1	1.341 (3)	C18—O7	1.202 (3)
C2—C3	1.484 (4)	C18—O8	1.340 (4)
C3—C10	1.386 (4)	C19—O8	1.457 (4)
C3—C4	1.395 (4)	C19—H19A	1.07 (4)
C4—C5	1.379 (4)	C19—H19B	1.00 (4)
C4—H4	0.96 (3)	C19—H19C	0.96 (4)
C5—C8	1.392 (4)	C20—H20	0.98 (3)
C5—C6	1.498 (4)	C41—C42	1.348 (7)
C6—O3	1.200 (3)	C41—C46	1.356 (5)
C6—O4	1.334 (3)	C41—H41	0.94 (5)
C7—O4	1.460 (4)	C42—C43	1.342 (7)
C7—H7A	1.07 (4)	C42—H42	1.01 (5)
C7—H7B	1.06 (4)	C43—C42ⁱ	1.342 (7)
C7—H7C	0.97 (4)	C43—H43	0.9500
C8—C9	1.407 (4)	C46—C41ⁱ	1.356 (5)
C8—H8	1.01 (3)	C46—H46	0.91 (5)
C9—C10	1.390 (4)	C47—C49	1.364 (5)
C9—C11	1.488 (4)	C47—C48	1.383 (5)
C10—H10	0.96 (3)	C47—H47	1.04 (4)
C11—C12	1.389 (4)	C48—C49ⁱⁱ	1.378 (5)
C11—C20	1.401 (4)	C48—H48	0.97 (4)
C12—C13	1.399 (4)	C49—C48ⁱⁱ	1.378 (5)
C12—H12	0.94 (2)	C49—H49	1.01 (4)
C13—C16	1.390 (4)	C53—C55	1.376 (5)
C13—C14	1.486 (4)	C53—C54	1.388 (5)
C14—O5	1.209 (3)	C53—H53	1.01 (3)
C14—O6	1.342 (3)	C54—C55ⁱⁱⁱ	1.375 (5)
C15—O6	1.450 (4)	C54—H54	0.93 (4)
C15—H15A	1.04 (4)	C55—C54ⁱⁱⁱ	1.375 (5)
C15—H15B	1.05 (4)	C55—H55	0.99 (3)

O1—C1—H1A	111 (2)	H15B—C15—H15C	112 (3)
O1—C1—H1B	105 (2)	C17—C16—C13	119.6 (3)
H1A—C1—H1B	109 (3)	C17—C16—H16	122.9 (18)
O1—C1—H1C	113 (2)	C13—C16—H16	117.4 (18)
H1A—C1—H1C	109 (3)	C20—C17—C16	120.2 (3)
H1B—C1—H1C	110 (3)	C20—C17—C18	118.1 (3)
O2—C2—O1	123.1 (3)	C16—C17—C18	121.7 (3)
O2—C2—C3	124.2 (3)	O7—C18—O8	123.8 (3)
O1—C2—C3	112.6 (3)	O7—C18—C17	124.5 (3)
C10—C3—C4	119.7 (3)	O8—C18—C17	111.7 (3)
C10—C3—C2	122.0 (2)	O8—C19—H19A	106 (2)
C4—C3—C2	118.2 (3)	O8—C19—H19B	108 (2)
C5—C4—C3	119.6 (3)	H19A—C19—H19B	106 (3)
C5—C4—H4	121.8 (16)	O8—C19—H19C	110 (2)
C3—C4—H4	118.6 (16)	H19A—C19—H19C	115 (3)
C4—C5—C8	120.4 (3)	H19B—C19—H19C	111 (3)
C4—C5—C6	122.4 (3)	C17—C20—C11	121.3 (3)
C8—C5—C6	117.1 (3)	C17—C20—H20	121.3 (15)
O3—C6—O4	124.2 (3)	C11—C20—H20	117.4 (16)
O3—C6—C5	123.9 (3)	C42—C41—C46	119.4 (5)
O4—C6—C5	111.9 (3)	C42—C41—H41	118 (3)
O4—C7—H7A	109 (2)	C46—C41—H41	122 (3)
O4—C7—H7B	103 (2)	C43—C42—C41	120.3 (5)
H7A—C7—H7B	112 (3)	C43—C42—H42	122 (3)
O4—C7—H7C	107 (2)	C41—C42—H42	117 (3)
H7A—C7—H7C	110 (3)	C42ⁱ—C43—C42	120.4 (6)
H7B—C7—H7C	116 (3)	C42ⁱ—C43—H43	119.8
C5—C8—C9	120.8 (3)	C42—C43—H43	119.8
C5—C8—H8	119.7 (16)	C41ⁱ—C46—C41	120.3 (6)
C9—C8—H8	119.4 (16)	C41ⁱ—C46—H46	119.9 (3)
C10—C9—C8	117.6 (3)	C41—C46—H46	119.9 (3)
C10—C9—C11	122.3 (2)	C49—C47—C48	119.3 (3)
C8—C9—C11	120.1 (3)	C49—C47—H47	120 (2)
C3—C10—C9	121.8 (3)	C48—C47—H47	121 (2)
C3—C10—H10	119.1 (18)	C49ⁱⁱ—C48—C47	120.2 (4)
C9—C10—H10	119.1 (18)	C49ⁱⁱ—C48—H48	123 (2)
C12—C11—C20	118.0 (3)	C47—C48—H48	116 (2)
C12—C11—C9	121.4 (2)	C47—C49—C48ⁱⁱ	120.5 (4)
C20—C11—C9	120.6 (3)	C47—C49—H49	118 (2)
C11—C12—C13	121.2 (3)	C48ⁱⁱ—C49—H49	122 (2)
C11—C12—H12	120.5 (16)	C55—C53—C54	120.2 (3)
C13—C12—H12	118.3 (16)	C55—C53—H53	120.6 (17)
C16—C13—C12	119.8 (3)	C54—C53—H53	119.2 (18)
C16—C13—C14	117.8 (3)	C55ⁱⁱⁱ—C54—C53	119.5 (3)
C12—C13—C14	122.4 (3)	C55ⁱⁱⁱ—C54—H54	122 (2)
O5—C14—O6	123.2 (3)	C53—C54—H54	119 (2)
O5—C14—C13	124.5 (3)	C54ⁱⁱⁱ—C55—C53	120.4 (3)
O6—C14—C13	112.3 (3)	C54ⁱⁱⁱ—C55—H55	120 (2)
O6—C15—H15A	111 (2)	C53—C55—H55	119 (2)
O6—C15—H15B	104 (2)	C2—O1—C1	116.3 (3)
H15A—C15—H15B	115 (3)	C6—O4—C7	115.3 (3)
O6—C15—H15C	108.1 (19)	C14—O6—C15	115.4 (3)
H15A—C15—H15C	106 (3)	C18—O8—C19	115.8 (3)

Symmetry codes: (i) −x, y, −z+1/2; (ii) −x, −y+1, −z; (iii) −x+1/2, −y+1/2, −z.

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