Tetrakis(4-carboxy­phenyl)­methane-di­methyl sulfoxide-toluene (1/4/1)

The title compound [systematic name: 4,4',4'',4'''-methanetetrayl­tetra­carboxyl­ic acid-di­methyl sulfoxide-toluene (1/4/1)], C₂₉H₂₀O₈, crystallizes from di­methyl sulfoxide (DMSO)/toluene to yield a structure in which the four carboxyl­ic acid groups of each mol­ecule donate a single hydrogen bond to the O atom of four mol­ecules of DMSO. Packing of the resulting aggregates, which have crystallographic twofold symmetry, leaves space for the inclusion of partially disordered mol­ecules of toluene, leading to the formation of crystals of overall composition tetrakis(4-carboxy­phenyl)­methane-di­methyl sulfoxide-toluene (1/4/1).

Key indicators

• Single-crystal X-ray study
• T = 225 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.066
• wR factor = 0.190
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms .....          6
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C27
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         S1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         S2
PLAT301_ALERT_3_C Main Residue  Disorder .........................       8.00 Perc.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: local Program; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997) and ATOMS (Shape Software, 2002); software used to prepare material for publication: SHELXTL.

4,4',4'',4'''-methanetetrayltetracarboxylic acid–dimethyl sulfoxide–toluene (1/4/1)

Crystal data

C29H20O8·C7H8·4C2H6OS	F(000) = 1904
Mr = 901.10	Dx = 1.283 Mg m^−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 28.723 (15) Å	θ = 20.0–21.0°
b = 7.269 (5) Å	µ = 2.36 mm^−1
c = 26.824 (9) Å	T = 225 K
β = 123.61 (3)°	Plate, colourless
V = 4664 (5) Å^3	0.50 × 0.14 × 0.06 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	3266 reflections with I > 2σ(I)
Radiation source: Sealed tube	Rint = 0.067
Graphite monochromator	θmax = 69.9°, θmin = 3.6°
ω/2θ scans	h = −34→34
Absorption correction: gaussian from crystal shape	k = −8→8
Tmin = 0.38, Tmax = 0.87	l = −32→32
32349 measured reflections	6 standard reflections every 60 min
4410 independent reflections	intensity decay: −3.9%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.066	H-atom parameters constrained
wR(F^2) = 0.190	w = 1/[σ^2(Fo^2) + (0.136P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
4410 reflections	Δρmax = 0.78 e Å^−3
295 parameters	Δρmin = −0.53 e Å^−3
46 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00030 (9)

Special details

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O11	0.13332 (11)	0.6814 (3)	0.16478 (11)	0.0570 (6)
H11	0.1492	0.7689	0.1602	0.086*
O12	0.15109 (13)	0.8442 (4)	0.24366 (13)	0.0771 (9)
O21	0.18517 (9)	−0.3172 (4)	0.47396 (11)	0.0698 (7)
H21	0.2007	−0.4051	0.4973	0.105*
O22	0.10910 (10)	−0.4599 (4)	0.45441 (13)	0.0855 (10)
C1	0.0000	0.1838 (5)	0.2500	0.0302 (7)
C11	0.03599 (9)	0.3131 (3)	0.23829 (11)	0.0304 (5)
C12	0.06745 (10)	0.4493 (3)	0.28079 (11)	0.0352 (5)
H12	0.0676	0.4552	0.3159	0.042*
C13	0.09833 (11)	0.5753 (3)	0.27201 (12)	0.0370 (6)
H13	0.1195	0.6653	0.3012	0.044*
C14	0.09827 (10)	0.5695 (3)	0.22038 (12)	0.0361 (6)
C15	0.06710 (11)	0.4352 (4)	0.17792 (12)	0.0387 (6)
H15	0.0669	0.4297	0.1428	0.046*
C16	0.03610 (11)	0.3085 (4)	0.18691 (12)	0.0361 (5)
H16	0.0150	0.2187	0.1576	0.043*
C17	0.13020 (12)	0.7133 (4)	0.21115 (14)	0.0454 (7)
C21	0.03653 (9)	0.0542 (3)	0.30335 (10)	0.0300 (5)
C22	0.09488 (10)	0.0563 (4)	0.33732 (11)	0.0365 (6)
H22	0.1136	0.1451	0.3292	0.044*
C23	0.12562 (10)	−0.0693 (4)	0.38261 (11)	0.0390 (6)
H23	0.1649	−0.0647	0.4049	0.047*
C24	0.09918 (10)	−0.2024 (3)	0.39557 (11)	0.0344 (5)
C25	0.04080 (11)	−0.2081 (3)	0.36102 (11)	0.0359 (5)
H25	0.0222	−0.2989	0.3686	0.043*
C26	0.01041 (10)	−0.0830 (3)	0.31628 (11)	0.0354 (5)
H26	−0.0288	−0.0891	0.2937	0.042*
C27	0.13093 (12)	−0.3395 (4)	0.44343 (12)	0.0431 (6)
S1	0.15401 (4)	0.14047 (12)	0.15068 (4)	0.0577 (3)
O1	0.17682 (11)	−0.0384 (3)	0.14387 (12)	0.0618 (7)
C18	0.1552 (3)	0.2920 (7)	0.1005 (3)	0.131 (3)
H18A	0.1272	0.2549	0.0598	0.197*
H18B	0.1919	0.2892	0.1068	0.197*
H18C	0.1472	0.4159	0.1072	0.197*
C19	0.2065 (2)	0.2339 (7)	0.2186 (2)	0.1067 (18)
H19A	0.2105	0.1618	0.2511	0.160*
H19B	0.1970	0.3597	0.2215	0.160*
H19C	0.2415	0.2325	0.2210	0.160*
S2	0.21912 (3)	0.30259 (12)	0.57796 (4)	0.0555 (3)
O2	0.24262 (9)	0.4438 (4)	0.55691 (12)	0.0760 (8)
C28	0.1833 (2)	0.1468 (6)	0.5187 (2)	0.0866 (13)
H28A	0.1491	0.2030	0.4865	0.130*
H28B	0.1744	0.0371	0.5324	0.130*
H28C	0.2067	0.1139	0.5043	0.130*
C29	0.27735 (18)	0.1653 (8)	0.6290 (3)	0.114 (2)
H29A	0.3021	0.2353	0.6652	0.171*
H29B	0.2973	0.1289	0.6110	0.171*
H29C	0.2645	0.0564	0.6390	0.171*
C31	0.0188 (4)	0.1043 (10)	0.5031 (4)	0.103 (2)	0.50
C32	0.0203 (4)	−0.0464 (13)	0.4722 (4)	0.111 (3)	0.50
H32	0.0378	−0.0364	0.4513	0.133*	0.50
C33	−0.0039 (4)	−0.2118 (11)	0.4722 (4)	0.127 (3)	0.50
H33	−0.0029	−0.3138	0.4513	0.152*	0.50
C34	−0.0298 (4)	−0.2266 (11)	0.5031 (5)	0.124 (4)	0.50
H34	−0.0462	−0.3384	0.5031	0.148*	0.50
C35	−0.0314 (4)	−0.0758 (14)	0.5340 (4)	0.110 (3)	0.50
H35	−0.0489	−0.0858	0.5549	0.132*	0.50
C36	−0.0071 (4)	0.0896 (12)	0.5340 (4)	0.101 (3)	0.50
H36	−0.0082	0.1915	0.5550	0.121*	0.50
C37	0.0450 (6)	0.283 (2)	0.5028 (6)	0.119 (4)	0.50
H37A	0.0210	0.3847	0.4981	0.178*	0.50
H37B	0.0499	0.2836	0.4698	0.178*	0.50
H37C	0.0811	0.2969	0.5402	0.178*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O11	0.0783 (16)	0.0404 (12)	0.0814 (15)	−0.0120 (11)	0.0625 (14)	−0.0041 (11)
O12	0.110 (2)	0.0585 (15)	0.099 (2)	−0.0453 (15)	0.0800 (19)	−0.0283 (14)
O21	0.0417 (12)	0.0660 (16)	0.0729 (16)	0.0027 (11)	0.0137 (11)	0.0345 (13)
O22	0.0521 (14)	0.0781 (19)	0.095 (2)	0.0008 (13)	0.0214 (13)	0.0536 (16)
C1	0.0270 (15)	0.0263 (16)	0.0356 (16)	0.000	0.0162 (13)	0.000
C11	0.0277 (11)	0.0237 (11)	0.0380 (12)	0.0014 (9)	0.0172 (10)	0.0027 (9)
C12	0.0378 (13)	0.0296 (12)	0.0405 (13)	−0.0006 (10)	0.0231 (11)	−0.0007 (10)
C13	0.0352 (12)	0.0270 (12)	0.0486 (14)	−0.0038 (10)	0.0230 (11)	−0.0037 (11)
C14	0.0339 (12)	0.0267 (12)	0.0516 (14)	0.0017 (10)	0.0260 (11)	0.0027 (11)
C15	0.0439 (14)	0.0356 (14)	0.0460 (14)	0.0026 (11)	0.0308 (12)	0.0016 (11)
C16	0.0353 (12)	0.0315 (13)	0.0429 (13)	−0.0025 (10)	0.0225 (11)	−0.0027 (10)
C17	0.0482 (15)	0.0358 (14)	0.0639 (18)	−0.0032 (12)	0.0385 (15)	−0.0008 (13)
C21	0.0285 (11)	0.0243 (11)	0.0342 (12)	−0.0015 (9)	0.0155 (10)	−0.0011 (9)
C22	0.0288 (12)	0.0321 (13)	0.0438 (13)	−0.0035 (10)	0.0171 (10)	0.0027 (11)
C23	0.0290 (12)	0.0389 (14)	0.0398 (13)	−0.0017 (10)	0.0133 (10)	0.0023 (11)
C24	0.0348 (12)	0.0293 (12)	0.0339 (12)	0.0001 (10)	0.0159 (10)	−0.0008 (10)
C25	0.0365 (13)	0.0302 (12)	0.0414 (13)	−0.0041 (10)	0.0218 (11)	0.0013 (10)
C26	0.0290 (11)	0.0314 (12)	0.0431 (13)	−0.0018 (10)	0.0183 (10)	0.0009 (11)
C27	0.0417 (14)	0.0403 (15)	0.0404 (13)	−0.0003 (12)	0.0183 (12)	0.0034 (12)
S1	0.0672 (5)	0.0434 (5)	0.0795 (6)	0.0047 (4)	0.0512 (5)	−0.0008 (4)
O1	0.0849 (17)	0.0354 (11)	0.1033 (19)	−0.0002 (11)	0.0759 (16)	−0.0010 (11)
C18	0.254 (8)	0.054 (3)	0.162 (6)	0.043 (4)	0.163 (6)	0.039 (3)
C19	0.083 (3)	0.077 (3)	0.122 (4)	0.006 (3)	0.033 (3)	−0.036 (3)
S2	0.0402 (4)	0.0555 (5)	0.0639 (5)	0.0012 (3)	0.0245 (4)	0.0107 (4)
O2	0.0386 (11)	0.0718 (17)	0.0859 (17)	−0.0020 (11)	0.0146 (11)	0.0406 (14)
C28	0.098 (3)	0.070 (3)	0.088 (3)	−0.014 (3)	0.049 (3)	−0.002 (2)
C29	0.054 (2)	0.133 (5)	0.138 (4)	0.023 (3)	0.043 (3)	0.092 (4)
C31	0.115 (5)	0.131 (6)	0.091 (4)	0.007 (5)	0.076 (3)	−0.012 (4)
C32	0.124 (5)	0.135 (7)	0.101 (4)	−0.004 (5)	0.079 (4)	−0.018 (5)
C33	0.133 (5)	0.142 (7)	0.112 (4)	−0.013 (5)	0.072 (4)	−0.016 (5)
C34	0.124 (6)	0.140 (7)	0.108 (5)	−0.011 (6)	0.066 (4)	−0.012 (5)
C35	0.116 (5)	0.136 (7)	0.096 (4)	−0.003 (5)	0.070 (4)	−0.010 (5)
C36	0.115 (5)	0.133 (6)	0.093 (4)	0.002 (5)	0.081 (3)	−0.008 (5)
C37	0.120 (7)	0.139 (9)	0.112 (7)	−0.003 (7)	0.074 (6)	0.001 (7)

Geometric parameters (Å, º)

O11—C17	1.316 (3)	S1—C19	1.735 (5)
O11—H11	0.8300	S1—C18	1.755 (5)
O12—C17	1.203 (4)	C18—H18A	0.9700
O21—C27	1.308 (4)	C18—H18B	0.9700
O21—H21	0.8300	C18—H18C	0.9700
O22—C27	1.204 (4)	C19—H19A	0.9700
C1—C21^i	1.541 (3)	C19—H19B	0.9700
C1—C21	1.541 (3)	C19—H19C	0.9700
C1—C11^i	1.552 (3)	S2—O2	1.500 (2)
C1—C11	1.552 (3)	S2—C28	1.748 (5)
C11—C16	1.380 (3)	S2—C29	1.770 (4)
C11—C12	1.398 (3)	C28—H28A	0.9700
C12—C13	1.383 (3)	C28—H28B	0.9700
C12—H12	0.9400	C28—H28C	0.9700
C13—C14	1.385 (4)	C29—H29A	0.9700
C13—H13	0.9400	C29—H29B	0.9700
C14—C15	1.387 (4)	C29—H29C	0.9700
C14—C17	1.499 (4)	C31—C32	1.3900
C15—C16	1.392 (3)	C31—C36	1.3900
C15—H15	0.9400	C31—C37	1.507 (15)
C16—H16	0.9400	C32—C33	1.3900
C21—C22	1.396 (3)	C32—H32	0.9400
C21—C26	1.402 (3)	C33—C34	1.3900
C22—C23	1.379 (4)	C33—H33	0.9400
C22—H22	0.9400	C34—C35	1.3900
C23—C24	1.388 (4)	C34—H34	0.9400
C23—H23	0.9400	C35—C36	1.3900
C24—C25	1.397 (4)	C35—H35	0.9400
C24—C27	1.475 (4)	C36—H36	0.9400
C25—C26	1.367 (4)	C37—H37A	0.9700
C25—H25	0.9400	C37—H37B	0.9700
C26—H26	0.9400	C37—H37C	0.9700
S1—O1	1.512 (2)
C17—O11—H11	109.5	O21—C27—C24	114.2 (2)
C27—O21—H21	109.5	O1—S1—C19	106.3 (2)
C21^i—C1—C21	104.6 (3)	O1—S1—C18	104.7 (2)
C21^i—C1—C11^i	111.75 (13)	C19—S1—C18	100.6 (3)
C21—C1—C11^i	111.69 (13)	S1—C18—H18A	109.5
C21^i—C1—C11	111.69 (13)	S1—C18—H18B	109.5
C21—C1—C11	111.75 (13)	H18A—C18—H18B	109.5
C11^i—C1—C11	105.5 (3)	S1—C18—H18C	109.5
C16—C11—C12	118.3 (2)	H18A—C18—H18C	109.5
C16—C11—C1	123.9 (2)	H18B—C18—H18C	109.5
C12—C11—C1	117.8 (2)	S1—C19—H19A	109.5
C13—C12—C11	121.1 (2)	S1—C19—H19B	109.5
C13—C12—H12	119.5	H19A—C19—H19B	109.5
C11—C12—H12	119.5	S1—C19—H19C	109.5
C12—C13—C14	120.3 (2)	H19A—C19—H19C	109.5
C12—C13—H13	119.9	H19B—C19—H19C	109.5
C14—C13—H13	119.9	O2—S2—C28	105.2 (2)
C13—C14—C15	119.1 (2)	O2—S2—C29	104.36 (18)
C13—C14—C17	118.8 (2)	C28—S2—C29	99.6 (3)
C15—C14—C17	122.1 (2)	S2—C28—H28A	109.5
C14—C15—C16	120.5 (2)	S2—C28—H28B	109.5
C14—C15—H15	119.7	H28A—C28—H28B	109.5
C16—C15—H15	119.7	S2—C28—H28C	109.5
C11—C16—C15	120.8 (2)	H28A—C28—H28C	109.5
C11—C16—H16	119.6	H28B—C28—H28C	109.5
C15—C16—H16	119.6	S2—C29—H29A	109.5
O12—C17—O11	123.9 (3)	S2—C29—H29B	109.5
O12—C17—C14	122.5 (3)	H29A—C29—H29B	109.5
O11—C17—C14	113.6 (2)	S2—C29—H29C	109.5
C22—C21—C26	117.4 (2)	H29A—C29—H29C	109.5
C22—C21—C1	123.6 (2)	H29B—C29—H29C	109.5
C26—C21—C1	118.8 (2)	C32—C31—C36	120.0
C23—C22—C21	121.3 (2)	C32—C31—C37	119.7 (9)
C23—C22—H22	119.3	C36—C31—C37	120.3 (9)
C21—C22—H22	119.3	C33—C32—C31	120.0
C22—C23—C24	120.7 (2)	C33—C32—H32	120.0
C22—C23—H23	119.7	C31—C32—H32	120.0
C24—C23—H23	119.7	C32—C33—C34	120.0
C23—C24—C25	118.5 (2)	C32—C33—H33	120.0
C23—C24—C27	121.9 (2)	C34—C33—H33	120.0
C25—C24—C27	119.6 (2)	C35—C34—C33	120.0
C26—C25—C24	120.8 (2)	C35—C34—H34	120.0
C26—C25—H25	119.6	C33—C34—H34	120.0
C24—C25—H25	119.6	C34—C35—C36	120.0
C25—C26—C21	121.4 (2)	C34—C35—H35	120.0
C25—C26—H26	119.3	C36—C35—H35	120.0
C21—C26—H26	119.3	C35—C36—C31	120.0
O22—C27—O21	122.5 (3)	C35—C36—H36	120.0
O22—C27—C24	123.3 (3)	C31—C36—H36	120.0
C21^i—C1—C11—C16	−1.5 (3)	C11^i—C1—C21—C26	68.0 (3)
C21—C1—C11—C16	115.3 (2)	C11—C1—C21—C26	−174.1 (2)
C11^i—C1—C11—C16	−123.2 (3)	C26—C21—C22—C23	−1.3 (4)
C21^i—C1—C11—C12	174.4 (2)	C1—C21—C22—C23	−176.5 (2)
C21—C1—C11—C12	−68.8 (3)	C21—C22—C23—C24	0.2 (4)
C11^i—C1—C11—C12	52.79 (17)	C22—C23—C24—C25	1.1 (4)
C16—C11—C12—C13	−0.6 (4)	C22—C23—C24—C27	179.5 (3)
C1—C11—C12—C13	−176.8 (2)	C23—C24—C25—C26	−1.3 (4)
C11—C12—C13—C14	0.5 (4)	C27—C24—C25—C26	−179.8 (2)
C12—C13—C14—C15	−0.3 (4)	C24—C25—C26—C21	0.2 (4)
C12—C13—C14—C17	177.3 (2)	C22—C21—C26—C25	1.1 (4)
C13—C14—C15—C16	0.3 (4)	C1—C21—C26—C25	176.5 (2)
C17—C14—C15—C16	−177.3 (2)	C23—C24—C27—O22	−177.7 (3)
C12—C11—C16—C15	0.5 (4)	C25—C24—C27—O22	0.7 (5)
C1—C11—C16—C15	176.5 (2)	C23—C24—C27—O21	3.6 (4)
C14—C15—C16—C11	−0.4 (4)	C25—C24—C27—O21	−178.0 (3)
C13—C14—C17—O12	−7.8 (4)	C36—C31—C32—C33	0.0
C15—C14—C17—O12	169.8 (3)	C37—C31—C32—C33	−179.8 (11)
C13—C14—C17—O11	171.7 (3)	C31—C32—C33—C34	0.0
C15—C14—C17—O11	−10.7 (4)	C32—C33—C34—C35	0.0
C21^i—C1—C21—C22	122.0 (3)	C33—C34—C35—C36	0.0
C11^i—C1—C21—C22	−116.9 (2)	C34—C35—C36—C31	0.0
C11—C1—C21—C22	1.0 (3)	C32—C31—C36—C35	0.0
C21^i—C1—C21—C26	−53.07 (18)	C37—C31—C36—C35	179.8 (11)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11···O1^ii	0.83	1.78	2.608 (3)	174
O21—H21···O2^iii	0.83	1.76	2.574 (3)	168

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