Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050672/hb2568sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050672/hb2568Isup2.hkl |
CCDC reference: 667202
Key indicators
- Single-crystal X-ray study
- T = 223 K
- Mean (C-C) = 0.005 Å
- Disorder in main residue
- R factor = 0.060
- wR factor = 0.181
- Data-to-parameter ratio = 20.5
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 5.80 Ratio
Author Response: There are two lattice molecules, a DMSO that lies on a general position, and a pyrazine that lies on a special position. There are no hydrogen bonds between either and the main molecule. Both can be treated as disordered molecules with the use of restraints, but this is not necessary. |
PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 7.33 Ratio
Author Response: As above. |
Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C27 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C31
Alert level C ABSMU01_ALERT_1_C The ratio of given/expected absorption coefficient lies outside the range 0.99 <> 1.01 Calculated value of mu = 0.776 Value of mu given = 0.797 DENSD01_ALERT_1_C The ratio of the submitted crystal density and that calculated from the formula is outside the range 0.99 <> 1.01 Crystal density given = 1.267 Calculated crystal density = 1.222 PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT044_ALERT_1_C Calculated and Reported Dx Differ .............. ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.25 Ratio PLAT046_ALERT_1_C Reported Z, MW and D(calc) are Inconsistent .... 1.22 PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.89 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms .. ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.35 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C19 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for S2 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N2 PLAT245_ALERT_2_C U(iso) H31D Smaller than U(eq) C32 by ... 0.04 AngSq PLAT245_ALERT_2_C U(iso) H31B Smaller than U(eq) C32' by ... 0.04 AngSq PLAT301_ALERT_3_C Main Residue Disorder ......................... 1.00 Perc. PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 60.00 Perc.
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C32.33 H53 N1.5 O7.67 S1.67 Atom count from _chemical_formula_moiety:C30.335 H49.675 N1.335 O7.1 FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C32.33 H53 N1.5 O7.67 S1.67 Zn Atom count from the _atom_site data: C32.34 H53.02 N1.5 O7.67 S1.67 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G ALERT: check formula stoichiometry or atom site occupancies. From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C32.33 H53 N1.50 O7.67 S1.67 Zn TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 129.32 129.36 -0.04 H 212.00 212.08 -0.08 N 6.00 6.00 0.00 O 30.68 30.68 0.00 S 6.68 6.68 0.00 Zn 4.00 4.00 0.00 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 105
2 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 19 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 11 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For other zinc terephthalate adducts of DMSO, see Wang et al. (2001) and Yang et al. (2005). For a report of the intercalation of DMSO in organic compounds, see Nangia & Desiraju (1999).
Pyrazine (0.4 mmol), tetra-n-butylammonium terephthalate (0.4 mmol), zinc nitrate hexahydrate (0.4 mmol) and dimethylsulfoxide (2 ml) was placed in a thin glass tube. The contents were set aside for a month for the formation of colourless blocks of (I).
There is some disorder in the terminal carbon atom of one of the four butyl chains of the cation. For the cation, the four N–C bonds were restrained to within 0.01 Å of each other as were the C–C distances. The C32 atom is disordered over two sites; the Uij values for C28 were set to those of C28'.
As one of the geometrically generated H atoms of the uncoordinated DMSO (S2/O8/C15/C16) molecule is too close to one of the geometrically generated H of the C28' atom, the occupancy of this DMSO molecule is not unity, and refining gave a value close to 0.667. Furthermore, the refinement of the occupancy of the C28/C28' pair of atoms gave a ratio of nearly 0.67/0.33. Consequently, the occupany of the DMSO was fixed as 2/3; the occupancy of C32 would then also be 2/3.
The pyrazine molecule lies on an inversion centre; its C—C and C—N bond distances were restrained to 1.35 (1) Å; the Uij values were restrained to be nearly isotropic. The carbon-bound H atoms were placed at calculated positions (C–H 0.93 to 0.98 Å) and were included in the refinement in the riding model approximation, with Uiso(H) = 1.2 to 1.5Ueq(C). The final difference Fourier map had a large peak in the vicinity of S1, but was otherwise essentially featureless.
Dimethyl sulfoxide (DMSO) occassionally gets trapped in organic molecular crystals through multi-point recognition between the solvent and molecule (Nangia & Desiraju, 1999). Similarly, coordination polymers synthesized using DMSO as solvent sometimes intercalate DMSO as solvated molecule (Wang et al., 2001, Yang et al., 2005). Our attempt to synthesize porous coordination polymers with the zinc ion, terephthalate dianion and pyrazine in DMSO resulted in the formation of the title compound, (I).
The zinc atom exists in a tetrahedral geometry (Table 1), being coordinated to one oxygen atom from a DMSO moleucle and three oxygen atoms from three different terephthalate anions (Fig. 1). The manner of bridging generates a wavy, honeycomb polyanionic layer (Figure 2). The space between adjacent layers is occupied by the bulky cation as well as the DMSO and pyrazine solvent molecules. The guest cations and molecules take up more than 60% of the unit cell volume. These guests interact with the layers through weak van der Waals interactions.
For other zinc terephthalate adducts of DMSO, see Wang et al. (2001) and Yang et al. (2005). For a report of the intercalation of DMSO in organic compounds, see Nangia & Desiraju (1999).
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001) and OLEX (Dolomanov et al., 2003); software used to prepare material for publication: publCIF (Westrip, 2007).
(C16H36N)[Zn(C8H4O4)1.5(C2H6OS)]·0.67C2H6OS·0.25C4H4N2 | F(000) = 1558 |
Mr = 704.26 | Dx = 1.267 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 6737 reflections |
a = 11.1722 (5) Å | θ = 2.2–27.6° |
b = 24.8188 (11) Å | µ = 0.80 mm−1 |
c = 13.9443 (6) Å | T = 223 K |
β = 97.968 (1)° | Irregular block, colorless |
V = 3829.2 (3) Å3 | 0.48 × 0.47 × 0.38 mm |
Z = 4 |
Bruker APEX area-detector diffractometer | 8752 independent reflections |
Radiation source: fine-focus sealed tube | 7451 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
φ and ω scans | θmax = 27.5°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→14 |
Tmin = 0.626, Tmax = 0.752 | k = −32→32 |
43211 measured reflections | l = −18→18 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.181 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.1092P)2 + 3.742P] where P = (Fo2 + 2Fc2)/3 |
8752 reflections | (Δ/σ)max = 0.001 |
427 parameters | Δρmax = 1.44 e Å−3 |
105 restraints | Δρmin = −0.61 e Å−3 |
(C16H36N)[Zn(C8H4O4)1.5(C2H6OS)]·0.67C2H6OS·0.25C4H4N2 | V = 3829.2 (3) Å3 |
Mr = 704.26 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.1722 (5) Å | µ = 0.80 mm−1 |
b = 24.8188 (11) Å | T = 223 K |
c = 13.9443 (6) Å | 0.48 × 0.47 × 0.38 mm |
β = 97.968 (1)° |
Bruker APEX area-detector diffractometer | 8752 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 7451 reflections with I > 2σ(I) |
Tmin = 0.626, Tmax = 0.752 | Rint = 0.038 |
43211 measured reflections |
R[F2 > 2σ(F2)] = 0.060 | 105 restraints |
wR(F2) = 0.181 | H-atom parameters constrained |
S = 1.05 | Δρmax = 1.44 e Å−3 |
8752 reflections | Δρmin = −0.61 e Å−3 |
427 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Zn1 | 0.64399 (3) | 0.642867 (13) | 0.33508 (2) | 0.02661 (13) | |
S1 | 0.38991 (8) | 0.57300 (4) | 0.32477 (7) | 0.0474 (2) | |
S2 | 0.5688 (3) | 0.98156 (14) | 0.66626 (17) | 0.1035 (8) | 0.67 |
O1 | 0.59927 (19) | 0.67880 (9) | 0.45005 (15) | 0.0349 (5) | |
O2 | 0.5151 (2) | 0.74012 (12) | 0.34659 (16) | 0.0518 (7) | |
O3 | 0.1890 (2) | 0.83652 (10) | 0.70662 (17) | 0.0425 (5) | |
O4 | 0.3049 (2) | 0.78816 (13) | 0.81478 (17) | 0.0531 (7) | |
O5 | 0.7673 (2) | 0.58738 (9) | 0.37480 (16) | 0.0396 (5) | |
O6 | 0.6877 (2) | 0.54688 (10) | 0.49407 (19) | 0.0460 (6) | |
O7 | 0.4824 (2) | 0.60747 (10) | 0.28330 (17) | 0.0445 (6) | |
O8 | 0.5191 (8) | 1.0295 (4) | 0.6328 (7) | 0.150 (4) | 0.67 |
N1 | 0.9806 (2) | 0.68523 (11) | 0.59716 (18) | 0.0379 (6) | |
C1 | 0.5326 (3) | 0.72000 (13) | 0.4272 (2) | 0.0333 (6) | |
C2 | 0.4686 (3) | 0.74255 (13) | 0.5077 (2) | 0.0326 (6) | |
C3 | 0.4834 (3) | 0.71959 (14) | 0.5987 (2) | 0.0406 (7) | |
H3 | 0.5360 | 0.6901 | 0.6122 | 0.049* | |
C4 | 0.4214 (3) | 0.73963 (15) | 0.6704 (2) | 0.0414 (7) | |
H4 | 0.4339 | 0.7242 | 0.7326 | 0.050* | |
C5 | 0.3412 (3) | 0.78209 (13) | 0.6515 (2) | 0.0330 (6) | |
C6 | 0.3251 (3) | 0.80457 (15) | 0.5598 (2) | 0.0422 (8) | |
H6 | 0.2704 | 0.8332 | 0.5457 | 0.051* | |
C7 | 0.3888 (3) | 0.78525 (15) | 0.4887 (2) | 0.0444 (8) | |
H7 | 0.3779 | 0.8012 | 0.4270 | 0.053* | |
C8 | 0.2740 (3) | 0.80337 (14) | 0.7308 (2) | 0.0380 (7) | |
C9 | 0.7701 (2) | 0.55514 (11) | 0.4462 (2) | 0.0302 (6) | |
C10 | 0.8894 (2) | 0.52593 (11) | 0.4732 (2) | 0.0284 (6) | |
C11 | 0.9800 (3) | 0.52863 (12) | 0.4141 (2) | 0.0319 (6) | |
H11 | 0.9665 | 0.5480 | 0.3556 | 0.038* | |
C12 | 1.0895 (3) | 0.50312 (12) | 0.4406 (2) | 0.0330 (6) | |
H12 | 1.1501 | 0.5054 | 0.4003 | 0.040* | |
C13 | 0.4011 (3) | 0.58585 (16) | 0.4505 (3) | 0.0484 (8) | |
H13A | 0.3699 | 0.6216 | 0.4607 | 0.073* | |
H13B | 0.4850 | 0.5838 | 0.4794 | 0.073* | |
H13C | 0.3543 | 0.5593 | 0.4803 | 0.073* | |
C14 | 0.4521 (4) | 0.50670 (17) | 0.3325 (3) | 0.0630 (11) | |
H14A | 0.4536 | 0.4926 | 0.2678 | 0.095* | |
H14B | 0.4028 | 0.4835 | 0.3671 | 0.095* | |
H14C | 0.5338 | 0.5079 | 0.3668 | 0.095* | |
C15 | 0.4521 (17) | 0.9380 (6) | 0.6315 (9) | 0.180 (8) | 0.67 |
H15A | 0.3880 | 0.9442 | 0.6705 | 0.270* | 0.67 |
H15B | 0.4807 | 0.9012 | 0.6404 | 0.270* | 0.67 |
H15C | 0.4213 | 0.9439 | 0.5637 | 0.270* | 0.67 |
C16 | 0.6612 (17) | 0.9648 (10) | 0.5953 (10) | 0.226 (11) | 0.67 |
H16A | 0.7320 | 0.9877 | 0.6065 | 0.339* | 0.67 |
H16B | 0.6231 | 0.9688 | 0.5288 | 0.339* | 0.67 |
H16C | 0.6850 | 0.9275 | 0.6070 | 0.339* | 0.67 |
C17 | 0.8735 (3) | 0.65174 (13) | 0.6193 (2) | 0.0385 (7) | |
H17A | 0.8038 | 0.6605 | 0.5711 | 0.046* | |
H17B | 0.8927 | 0.6137 | 0.6109 | 0.046* | |
C18 | 0.8364 (4) | 0.65861 (16) | 0.7188 (3) | 0.0487 (9) | |
H18A | 0.8068 | 0.6953 | 0.7263 | 0.058* | |
H18B | 0.9058 | 0.6524 | 0.7687 | 0.058* | |
C19 | 0.7367 (3) | 0.61794 (15) | 0.7296 (3) | 0.0486 (8) | |
H19A | 0.6725 | 0.6218 | 0.6745 | 0.058* | |
H19B | 0.7699 | 0.5815 | 0.7272 | 0.058* | |
C20 | 0.6817 (5) | 0.6240 (2) | 0.8225 (4) | 0.0817 (16) | |
H20A | 0.6194 | 0.5970 | 0.8246 | 0.123* | |
H20B | 0.6465 | 0.6596 | 0.8249 | 0.123* | |
H20C | 0.7441 | 0.6193 | 0.8776 | 0.123* | |
C21 | 0.9985 (3) | 0.66980 (14) | 0.4949 (2) | 0.0410 (7) | |
H21A | 1.0147 | 0.6310 | 0.4942 | 0.049* | |
H21B | 0.9219 | 0.6759 | 0.4528 | 0.049* | |
C22 | 1.0968 (3) | 0.69794 (15) | 0.4500 (2) | 0.0471 (8) | |
H22A | 1.1731 | 0.6963 | 0.4940 | 0.056* | |
H22B | 1.0755 | 0.7359 | 0.4382 | 0.056* | |
C23 | 1.1112 (3) | 0.67031 (16) | 0.3550 (2) | 0.0466 (8) | |
H23A | 1.0320 | 0.6682 | 0.3150 | 0.056* | |
H23B | 1.1399 | 0.6334 | 0.3686 | 0.056* | |
C24 | 1.1989 (4) | 0.6992 (2) | 0.2981 (3) | 0.0621 (11) | |
H24A | 1.2036 | 0.6800 | 0.2381 | 0.093* | |
H24B | 1.2783 | 0.7004 | 0.3363 | 0.093* | |
H24C | 1.1706 | 0.7357 | 0.2835 | 0.093* | |
C25 | 1.0928 (3) | 0.67370 (15) | 0.6683 (3) | 0.0476 (8) | |
H25A | 1.0782 | 0.6854 | 0.7328 | 0.057* | |
H25B | 1.1594 | 0.6955 | 0.6503 | 0.057* | |
C26 | 1.1329 (4) | 0.61516 (19) | 0.6747 (4) | 0.0784 (15) | |
H26A | 1.0694 | 0.5929 | 0.6963 | 0.094* | |
H26B | 1.1470 | 0.6024 | 0.6107 | 0.094* | |
C27 | 1.2475 (5) | 0.6102 (3) | 0.7453 (5) | 0.111 (2) | |
H27A | 1.3083 | 0.6344 | 0.7244 | 0.133* | |
H27B | 1.2311 | 0.6227 | 0.8089 | 0.133* | |
C28 | 1.2987 (10) | 0.5555 (4) | 0.7559 (10) | 0.224 (7) | |
H28A | 1.3708 | 0.5559 | 0.8035 | 0.337* | |
H28B | 1.3193 | 0.5434 | 0.6941 | 0.337* | |
H28C | 1.2397 | 0.5312 | 0.7772 | 0.337* | |
C29 | 0.9563 (3) | 0.74534 (13) | 0.6051 (2) | 0.0433 (8) | |
H29A | 0.9532 | 0.7541 | 0.6732 | 0.052* | |
H29B | 1.0244 | 0.7652 | 0.5848 | 0.052* | |
C30 | 0.8404 (3) | 0.76503 (14) | 0.5455 (3) | 0.0507 (9) | |
H30A | 0.7707 | 0.7515 | 0.5737 | 0.061* | |
H30B | 0.8353 | 0.7509 | 0.4794 | 0.061* | |
C31 | 0.8365 (5) | 0.82621 (16) | 0.5425 (4) | 0.0676 (12) | |
H31A | 0.8426 | 0.8399 | 0.6088 | 0.081* | 0.33 |
H31B | 0.7583 | 0.8377 | 0.5078 | 0.081* | 0.33 |
H31C | 0.8578 | 0.8406 | 0.6080 | 0.081* | 0.67 |
H31D | 0.8956 | 0.8396 | 0.5025 | 0.081* | 0.67 |
C32 | 0.9368 (9) | 0.8511 (4) | 0.4936 (10) | 0.124 (4) | 0.67 |
H32A | 0.9296 | 0.8900 | 0.4941 | 0.186* | 0.67 |
H32B | 0.9302 | 0.8385 | 0.4272 | 0.186* | 0.67 |
H32C | 1.0146 | 0.8406 | 0.5282 | 0.186* | 0.67 |
C32' | 0.7109 (11) | 0.8452 (9) | 0.501 (2) | 0.124 (4) | 0.33 |
H32D | 0.7092 | 0.8843 | 0.4991 | 0.186* | 0.33 |
H32E | 0.6527 | 0.8322 | 0.5409 | 0.186* | 0.33 |
H32F | 0.6905 | 0.8313 | 0.4355 | 0.186* | 0.33 |
N2 | 0.4355 (13) | 0.5001 (6) | 0.0732 (9) | 0.121 (4) | 0.50 |
C33 | 0.5243 (17) | 0.5325 (8) | 0.0698 (14) | 0.143 (6) | 0.50 |
H33 | 0.5428 | 0.5581 | 0.1193 | 0.171* | 0.50 |
C34 | 0.415 (2) | 0.4692 (8) | −0.0040 (14) | 0.160 (7) | 0.50 |
H34 | 0.3468 | 0.4465 | −0.0087 | 0.192* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.02605 (19) | 0.0307 (2) | 0.02437 (19) | 0.00432 (12) | 0.00790 (13) | 0.00481 (11) |
S1 | 0.0347 (4) | 0.0568 (5) | 0.0500 (5) | −0.0105 (4) | 0.0032 (4) | 0.0037 (4) |
S2 | 0.122 (2) | 0.121 (2) | 0.0642 (13) | −0.0155 (17) | 0.0000 (13) | −0.0061 (13) |
O1 | 0.0355 (11) | 0.0379 (11) | 0.0336 (11) | 0.0072 (9) | 0.0129 (9) | −0.0017 (9) |
O2 | 0.0593 (15) | 0.0694 (17) | 0.0298 (12) | 0.0266 (13) | 0.0177 (11) | 0.0070 (11) |
O3 | 0.0408 (12) | 0.0531 (14) | 0.0364 (12) | −0.0006 (11) | 0.0155 (10) | −0.0137 (10) |
O4 | 0.0504 (14) | 0.0816 (19) | 0.0298 (12) | −0.0007 (13) | 0.0150 (10) | −0.0096 (12) |
O5 | 0.0367 (11) | 0.0418 (12) | 0.0417 (12) | 0.0163 (9) | 0.0103 (9) | 0.0117 (10) |
O6 | 0.0299 (11) | 0.0521 (14) | 0.0580 (15) | 0.0089 (10) | 0.0130 (10) | 0.0165 (12) |
O7 | 0.0396 (12) | 0.0562 (15) | 0.0369 (12) | −0.0133 (11) | 0.0029 (10) | 0.0057 (10) |
O8 | 0.117 (6) | 0.156 (8) | 0.166 (8) | 0.031 (6) | −0.015 (6) | −0.084 (7) |
N1 | 0.0393 (14) | 0.0420 (15) | 0.0326 (13) | −0.0105 (11) | 0.0052 (11) | −0.0086 (11) |
C1 | 0.0305 (14) | 0.0401 (16) | 0.0309 (15) | 0.0048 (12) | 0.0099 (11) | −0.0010 (12) |
C2 | 0.0324 (14) | 0.0384 (16) | 0.0280 (14) | 0.0042 (12) | 0.0079 (11) | −0.0014 (11) |
C3 | 0.0427 (17) | 0.0472 (18) | 0.0334 (16) | 0.0118 (14) | 0.0104 (13) | 0.0022 (13) |
C4 | 0.0436 (18) | 0.056 (2) | 0.0264 (14) | 0.0049 (15) | 0.0098 (13) | 0.0029 (13) |
C5 | 0.0288 (14) | 0.0431 (17) | 0.0286 (14) | −0.0046 (12) | 0.0092 (11) | −0.0096 (12) |
C6 | 0.0461 (18) | 0.0479 (19) | 0.0347 (16) | 0.0172 (15) | 0.0126 (14) | 0.0006 (14) |
C7 | 0.055 (2) | 0.052 (2) | 0.0281 (15) | 0.0188 (16) | 0.0132 (14) | 0.0054 (13) |
C8 | 0.0319 (15) | 0.0488 (18) | 0.0354 (16) | −0.0121 (13) | 0.0119 (12) | −0.0157 (13) |
C9 | 0.0274 (13) | 0.0252 (13) | 0.0378 (15) | 0.0023 (10) | 0.0037 (11) | −0.0016 (11) |
C10 | 0.0258 (12) | 0.0233 (12) | 0.0365 (15) | 0.0015 (10) | 0.0055 (11) | 0.0000 (10) |
C11 | 0.0339 (14) | 0.0291 (14) | 0.0335 (14) | 0.0056 (11) | 0.0080 (12) | 0.0066 (11) |
C12 | 0.0309 (14) | 0.0314 (14) | 0.0387 (15) | 0.0043 (11) | 0.0125 (12) | 0.0046 (12) |
C13 | 0.0408 (18) | 0.054 (2) | 0.054 (2) | −0.0038 (15) | 0.0181 (16) | 0.0072 (17) |
C14 | 0.069 (3) | 0.049 (2) | 0.074 (3) | −0.012 (2) | 0.019 (2) | −0.006 (2) |
C15 | 0.26 (2) | 0.166 (13) | 0.096 (9) | −0.097 (14) | −0.041 (11) | 0.013 (8) |
C16 | 0.23 (2) | 0.34 (3) | 0.098 (10) | 0.12 (2) | 0.002 (11) | 0.045 (14) |
C17 | 0.0384 (16) | 0.0379 (16) | 0.0398 (17) | −0.0107 (13) | 0.0070 (13) | −0.0077 (13) |
C18 | 0.055 (2) | 0.049 (2) | 0.0441 (19) | −0.0156 (17) | 0.0165 (16) | −0.0104 (15) |
C19 | 0.050 (2) | 0.0446 (19) | 0.053 (2) | −0.0083 (16) | 0.0139 (16) | −0.0013 (16) |
C20 | 0.095 (4) | 0.082 (3) | 0.078 (3) | −0.040 (3) | 0.047 (3) | −0.017 (3) |
C21 | 0.0430 (17) | 0.0466 (19) | 0.0340 (16) | −0.0096 (14) | 0.0078 (13) | −0.0116 (13) |
C22 | 0.0471 (19) | 0.052 (2) | 0.0436 (19) | −0.0092 (16) | 0.0125 (15) | −0.0061 (15) |
C23 | 0.0387 (17) | 0.058 (2) | 0.0449 (19) | 0.0006 (15) | 0.0111 (15) | −0.0018 (16) |
C24 | 0.055 (2) | 0.077 (3) | 0.058 (2) | 0.001 (2) | 0.0230 (19) | 0.005 (2) |
C25 | 0.0404 (18) | 0.059 (2) | 0.0416 (18) | −0.0096 (16) | −0.0001 (14) | −0.0061 (16) |
C26 | 0.060 (3) | 0.073 (3) | 0.094 (4) | 0.012 (2) | −0.017 (3) | −0.007 (3) |
C27 | 0.089 (5) | 0.098 (5) | 0.133 (6) | 0.014 (4) | −0.029 (4) | 0.010 (4) |
C28 | 0.152 (9) | 0.199 (12) | 0.287 (16) | 0.094 (9) | −0.093 (10) | −0.078 (11) |
C29 | 0.0515 (19) | 0.0412 (18) | 0.0379 (17) | −0.0113 (15) | 0.0091 (14) | −0.0084 (14) |
C30 | 0.060 (2) | 0.046 (2) | 0.046 (2) | −0.0014 (17) | 0.0043 (17) | −0.0071 (15) |
C31 | 0.089 (3) | 0.045 (2) | 0.070 (3) | 0.001 (2) | 0.015 (2) | 0.004 (2) |
C32 | 0.123 (8) | 0.094 (7) | 0.154 (10) | 0.011 (6) | 0.018 (7) | 0.054 (6) |
C32' | 0.123 (8) | 0.094 (7) | 0.154 (10) | 0.011 (6) | 0.018 (7) | 0.054 (6) |
N2 | 0.147 (8) | 0.129 (8) | 0.090 (6) | −0.034 (7) | 0.027 (6) | −0.004 (6) |
C33 | 0.163 (10) | 0.151 (10) | 0.117 (9) | −0.015 (8) | 0.031 (8) | 0.029 (8) |
C34 | 0.172 (11) | 0.167 (11) | 0.142 (10) | −0.029 (9) | 0.029 (9) | 0.017 (9) |
Zn1—O1 | 1.959 (2) | C18—H18A | 0.9800 |
Zn1—O5 | 1.972 (2) | C18—H18B | 0.9800 |
Zn1—O3i | 1.993 (2) | C19—C20 | 1.516 (5) |
Zn1—O7 | 2.047 (2) | C19—H19A | 0.9800 |
S1—O7 | 1.516 (2) | C19—H19B | 0.9800 |
S1—C13 | 1.769 (4) | C20—H20A | 0.9700 |
S1—C14 | 1.784 (5) | C20—H20B | 0.9700 |
S2—O8 | 1.368 (10) | C20—H20C | 0.9700 |
S2—C16 | 1.581 (17) | C21—C22 | 1.509 (4) |
S2—C15 | 1.712 (13) | C21—H21A | 0.9800 |
O1—C1 | 1.279 (4) | C21—H21B | 0.9800 |
O2—C1 | 1.220 (4) | C22—C23 | 1.519 (4) |
O3—C8 | 1.266 (4) | C22—H22A | 0.9800 |
O3—Zn1ii | 1.993 (2) | C22—H22B | 0.9800 |
O4—C8 | 1.234 (4) | C23—C24 | 1.524 (4) |
O5—C9 | 1.274 (4) | C23—H23A | 0.9800 |
O6—C9 | 1.228 (4) | C23—H23B | 0.9800 |
N1—C25 | 1.515 (4) | C24—H24A | 0.9700 |
N1—C21 | 1.517 (4) | C24—H24B | 0.9700 |
N1—C17 | 1.523 (4) | C24—H24C | 0.9700 |
N1—C29 | 1.523 (4) | C25—C26 | 1.519 (5) |
C1—C2 | 1.519 (4) | C25—H25A | 0.9800 |
C2—C3 | 1.380 (4) | C25—H25B | 0.9800 |
C2—C7 | 1.387 (4) | C26—C27 | 1.508 (5) |
C3—C4 | 1.385 (4) | C26—H26A | 0.9800 |
C3—H3 | 0.9400 | C26—H26B | 0.9800 |
C4—C5 | 1.385 (5) | C27—C28 | 1.473 (7) |
C4—H4 | 0.9400 | C27—H27A | 0.9800 |
C5—C6 | 1.383 (4) | C27—H27B | 0.9800 |
C5—C8 | 1.516 (4) | C28—H28A | 0.9700 |
C6—C7 | 1.384 (4) | C28—H28B | 0.9700 |
C6—H6 | 0.9400 | C28—H28C | 0.9700 |
C7—H7 | 0.9400 | C29—C30 | 1.519 (4) |
C8—Zn1ii | 2.567 (3) | C29—H29A | 0.9800 |
C9—C10 | 1.518 (4) | C29—H29B | 0.9800 |
C10—C11 | 1.392 (4) | C30—C31 | 1.519 (5) |
C10—C12iii | 1.393 (4) | C30—H30A | 0.9800 |
C11—C12 | 1.382 (4) | C30—H30B | 0.9800 |
C11—H11 | 0.9400 | C31—C32' | 1.518 (8) |
C12—C10iii | 1.393 (4) | C31—C32 | 1.520 (7) |
C12—H12 | 0.9400 | C31—H31A | 0.9800 |
C13—H13A | 0.9700 | C31—H31B | 0.9800 |
C13—H13B | 0.9700 | C31—H31C | 0.9800 |
C13—H13C | 0.9700 | C31—H31D | 0.9800 |
C14—H14A | 0.9700 | C32—H32A | 0.9700 |
C14—H14B | 0.9700 | C32—H32B | 0.9700 |
C14—H14C | 0.9700 | C32—H32C | 0.9700 |
C15—H15A | 0.9700 | C32'—H32D | 0.9700 |
C15—H15B | 0.9700 | C32'—H32E | 0.9700 |
C15—H15C | 0.9700 | C32'—H32F | 0.9700 |
C16—H16A | 0.9700 | N2—C33 | 1.283 (15) |
C16—H16B | 0.9700 | N2—C34 | 1.316 (15) |
C16—H16C | 0.9700 | C33—C34iv | 1.218 (16) |
C17—C18 | 1.511 (4) | C33—H33 | 0.9400 |
C17—H17A | 0.9800 | C34—C33iv | 1.218 (16) |
C17—H17B | 0.9800 | C34—H34 | 0.9400 |
C18—C19 | 1.526 (4) | ||
O1—Zn1—O5 | 109.61 (9) | C18—C19—H19B | 108.8 |
O1—Zn1—O3i | 138.01 (10) | H19A—C19—H19B | 107.6 |
O5—Zn1—O3i | 100.27 (10) | C19—C20—H20A | 109.5 |
O1—Zn1—O7 | 99.87 (10) | C19—C20—H20B | 109.5 |
O5—Zn1—O7 | 110.29 (10) | H20A—C20—H20B | 109.5 |
O3i—Zn1—O7 | 96.49 (10) | C19—C20—H20C | 109.5 |
O7—S1—C13 | 108.55 (16) | H20A—C20—H20C | 109.5 |
O7—S1—C14 | 105.26 (19) | H20B—C20—H20C | 109.5 |
C13—S1—C14 | 97.7 (2) | C22—C21—N1 | 118.2 (3) |
O8—S2—C16 | 106.6 (9) | C22—C21—H21A | 107.8 |
O8—S2—C15 | 101.3 (7) | N1—C21—H21A | 107.8 |
C16—S2—C15 | 101.2 (11) | C22—C21—H21B | 107.8 |
C1—O1—Zn1 | 111.44 (18) | N1—C21—H21B | 107.8 |
C8—O3—Zn1ii | 101.6 (2) | H21A—C21—H21B | 107.1 |
C9—O5—Zn1 | 126.77 (19) | C21—C22—C23 | 108.9 (3) |
S1—O7—Zn1 | 136.20 (14) | C21—C22—H22A | 109.9 |
C25—N1—C21 | 111.3 (3) | C23—C22—H22A | 109.9 |
C25—N1—C17 | 111.5 (3) | C21—C22—H22B | 109.9 |
C21—N1—C17 | 105.2 (2) | C23—C22—H22B | 109.9 |
C25—N1—C29 | 106.1 (2) | H22A—C22—H22B | 108.3 |
C21—N1—C29 | 111.3 (3) | C22—C23—C24 | 113.3 (3) |
C17—N1—C29 | 111.5 (2) | C22—C23—H23A | 108.9 |
O2—C1—O1 | 124.8 (3) | C24—C23—H23A | 108.9 |
O2—C1—C2 | 119.9 (3) | C22—C23—H23B | 108.9 |
O1—C1—C2 | 115.3 (3) | C24—C23—H23B | 108.9 |
C3—C2—C7 | 118.9 (3) | H23A—C23—H23B | 107.7 |
C3—C2—C1 | 121.3 (3) | C23—C24—H24A | 109.5 |
C7—C2—C1 | 119.7 (3) | C23—C24—H24B | 109.5 |
C2—C3—C4 | 120.5 (3) | H24A—C24—H24B | 109.5 |
C2—C3—H3 | 119.8 | C23—C24—H24C | 109.5 |
C4—C3—H3 | 119.8 | H24A—C24—H24C | 109.5 |
C5—C4—C3 | 120.7 (3) | H24B—C24—H24C | 109.5 |
C5—C4—H4 | 119.7 | N1—C25—C26 | 115.4 (3) |
C3—C4—H4 | 119.7 | N1—C25—H25A | 108.4 |
C6—C5—C4 | 118.8 (3) | C26—C25—H25A | 108.4 |
C6—C5—C8 | 121.3 (3) | N1—C25—H25B | 108.4 |
C4—C5—C8 | 119.9 (3) | C26—C25—H25B | 108.4 |
C5—C6—C7 | 120.5 (3) | H25A—C25—H25B | 107.5 |
C5—C6—H6 | 119.7 | C27—C26—C25 | 109.4 (4) |
C7—C6—H6 | 119.7 | C27—C26—H26A | 109.8 |
C6—C7—C2 | 120.6 (3) | C25—C26—H26A | 109.8 |
C6—C7—H7 | 119.7 | C27—C26—H26B | 109.8 |
C2—C7—H7 | 119.7 | C25—C26—H26B | 109.8 |
O4—C8—O3 | 123.5 (3) | H26A—C26—H26B | 108.2 |
O4—C8—C5 | 119.0 (3) | C28—C27—C26 | 115.0 (6) |
O3—C8—C5 | 117.5 (3) | C28—C27—H27A | 108.5 |
O4—C8—Zn1ii | 74.17 (18) | C26—C27—H27A | 108.5 |
O3—C8—Zn1ii | 49.51 (14) | C28—C27—H27B | 108.5 |
C5—C8—Zn1ii | 166.2 (3) | C26—C27—H27B | 108.5 |
O6—C9—O5 | 126.2 (3) | H27A—C27—H27B | 107.5 |
O6—C9—C10 | 119.0 (3) | C27—C28—H28A | 109.5 |
O5—C9—C10 | 114.8 (2) | C27—C28—H28B | 109.5 |
C11—C10—C12iii | 119.1 (3) | H28A—C28—H28B | 109.5 |
C11—C10—C9 | 121.0 (3) | C27—C28—H28C | 109.5 |
C12iii—C10—C9 | 119.9 (3) | H28A—C28—H28C | 109.5 |
C12—C11—C10 | 120.5 (3) | H28B—C28—H28C | 109.5 |
C12—C11—H11 | 119.7 | C30—C29—N1 | 115.0 (3) |
C10—C11—H11 | 119.7 | C30—C29—H29A | 108.5 |
C11—C12—C10iii | 120.4 (3) | N1—C29—H29A | 108.5 |
C11—C12—H12 | 119.8 | C30—C29—H29B | 108.5 |
C10iii—C12—H12 | 119.8 | N1—C29—H29B | 108.5 |
S1—C13—H13A | 109.5 | H29A—C29—H29B | 107.5 |
S1—C13—H13B | 109.5 | C29—C30—C31 | 110.8 (3) |
H13A—C13—H13B | 109.5 | C29—C30—H30A | 109.5 |
S1—C13—H13C | 109.5 | C31—C30—H30A | 109.5 |
H13A—C13—H13C | 109.5 | C29—C30—H30B | 109.5 |
H13B—C13—H13C | 109.5 | C31—C30—H30B | 109.5 |
S1—C14—H14A | 109.5 | H30A—C30—H30B | 108.1 |
S1—C14—H14B | 109.5 | C32'—C31—C30 | 110.0 (10) |
H14A—C14—H14B | 109.5 | C32'—C31—C32 | 113.7 (10) |
S1—C14—H14C | 109.5 | C30—C31—C32 | 113.4 (6) |
H14A—C14—H14C | 109.5 | C30—C31—H31A | 108.9 |
H14B—C14—H14C | 109.5 | C32—C31—H31A | 108.9 |
S2—C15—H15A | 109.5 | C30—C31—H31B | 108.9 |
S2—C15—H15B | 109.5 | C32—C31—H31B | 108.9 |
H15A—C15—H15B | 109.5 | H31A—C31—H31B | 107.7 |
S2—C15—H15C | 109.5 | C32'—C31—H31C | 109.7 |
H15A—C15—H15C | 109.5 | C30—C31—H31C | 109.7 |
H15B—C15—H15C | 109.5 | C32'—C31—H31D | 109.7 |
S2—C16—H16A | 109.5 | C30—C31—H31D | 109.7 |
S2—C16—H16B | 109.5 | H31C—C31—H31D | 108.2 |
H16A—C16—H16B | 109.5 | C31—C32—H32A | 109.5 |
S2—C16—H16C | 109.5 | C31—C32—H32B | 109.5 |
H16A—C16—H16C | 109.5 | H32A—C32—H32B | 109.5 |
H16B—C16—H16C | 109.5 | C31—C32—H32C | 109.5 |
C18—C17—N1 | 116.6 (3) | H32A—C32—H32C | 109.5 |
C18—C17—H17A | 108.1 | H32B—C32—H32C | 109.5 |
N1—C17—H17A | 108.1 | C31—C32'—H32D | 109.5 |
C18—C17—H17B | 108.1 | C31—C32'—H32E | 109.5 |
N1—C17—H17B | 108.1 | H32D—C32'—H32E | 109.5 |
H17A—C17—H17B | 107.3 | C31—C32'—H32F | 109.5 |
C17—C18—C19 | 108.3 (3) | H32D—C32'—H32F | 109.5 |
C17—C18—H18A | 110.0 | H32E—C32'—H32F | 109.5 |
C19—C18—H18A | 110.0 | C33—N2—C34 | 112.6 (14) |
C17—C18—H18B | 110.0 | C34iv—C33—N2 | 121 (2) |
C19—C18—H18B | 110.0 | C34iv—C33—H33 | 119.3 |
H18A—C18—H18B | 108.4 | N2—C33—H33 | 119.3 |
C20—C19—C18 | 114.0 (3) | C33iv—C34—N2 | 126 (2) |
C20—C19—H19A | 108.8 | C33iv—C34—H34 | 117.1 |
C18—C19—H19A | 108.8 | N2—C34—H34 | 117.1 |
C20—C19—H19B | 108.8 | ||
O5—Zn1—O1—C1 | 170.8 (2) | C6—C5—C8—Zn1ii | −7.4 (11) |
O3i—Zn1—O1—C1 | 38.0 (3) | C4—C5—C8—Zn1ii | 172.1 (7) |
O7—Zn1—O1—C1 | −73.4 (2) | Zn1—O5—C9—O6 | 12.2 (5) |
C8i—Zn1—O1—C1 | 63.7 (2) | Zn1—O5—C9—C10 | −166.51 (19) |
O1—Zn1—O5—C9 | 40.6 (3) | O6—C9—C10—C11 | 171.8 (3) |
O3i—Zn1—O5—C9 | −169.3 (3) | O5—C9—C10—C11 | −9.4 (4) |
O7—Zn1—O5—C9 | −68.4 (3) | O6—C9—C10—C12iii | −9.7 (4) |
C13—S1—O7—Zn1 | 25.2 (3) | O5—C9—C10—C12iii | 169.1 (3) |
C14—S1—O7—Zn1 | −78.6 (3) | C12iii—C10—C11—C12 | −0.4 (5) |
O1—Zn1—O7—S1 | −49.4 (3) | C9—C10—C11—C12 | 178.2 (3) |
O5—Zn1—O7—S1 | 65.9 (3) | C10—C11—C12—C10iii | 0.4 (5) |
O3i—Zn1—O7—S1 | 169.4 (2) | C25—N1—C17—C18 | 58.4 (4) |
Zn1—O1—C1—O2 | −11.5 (4) | C21—N1—C17—C18 | 179.2 (3) |
Zn1—O1—C1—C2 | 165.9 (2) | C29—N1—C17—C18 | −60.0 (4) |
O2—C1—C2—C3 | 177.8 (3) | N1—C17—C18—C19 | −174.6 (3) |
O1—C1—C2—C3 | 0.3 (5) | C17—C18—C19—C20 | −174.2 (4) |
O2—C1—C2—C7 | 1.2 (5) | C25—N1—C21—C22 | −61.2 (4) |
O1—C1—C2—C7 | −176.3 (3) | C17—N1—C21—C22 | 178.0 (3) |
C7—C2—C3—C4 | −1.3 (5) | C29—N1—C21—C22 | 57.0 (4) |
C1—C2—C3—C4 | −177.9 (3) | N1—C21—C22—C23 | 171.3 (3) |
C2—C3—C4—C5 | 1.7 (5) | C21—C22—C23—C24 | 173.8 (3) |
C3—C4—C5—C6 | −0.7 (5) | C21—N1—C25—C26 | −60.2 (4) |
C3—C4—C5—C8 | 179.8 (3) | C17—N1—C25—C26 | 57.0 (4) |
C4—C5—C6—C7 | −0.6 (5) | C29—N1—C25—C26 | 178.6 (4) |
C8—C5—C6—C7 | 178.9 (3) | N1—C25—C26—C27 | 178.0 (5) |
C5—C6—C7—C2 | 0.9 (6) | C25—C26—C27—C28 | −178.0 (9) |
C3—C2—C7—C6 | 0.0 (6) | C25—N1—C29—C30 | −175.0 (3) |
C1—C2—C7—C6 | 176.7 (3) | C21—N1—C29—C30 | 63.8 (4) |
Zn1ii—O3—C8—O4 | 4.9 (4) | C17—N1—C29—C30 | −53.5 (4) |
Zn1ii—O3—C8—C5 | −174.4 (2) | N1—C29—C30—C31 | −168.9 (3) |
C6—C5—C8—O4 | −168.5 (3) | C29—C30—C31—C32' | −168.5 (12) |
C4—C5—C8—O4 | 10.9 (5) | C29—C30—C31—C32 | 62.9 (8) |
C6—C5—C8—O3 | 10.8 (5) | C34—N2—C33—C34iv | −5 (4) |
C4—C5—C8—O3 | −169.7 (3) | C33—N2—C34—C33iv | 5 (4) |
Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) x−1/2, −y+3/2, z+1/2; (iii) −x+2, −y+1, −z+1; (iv) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | (C16H36N)[Zn(C8H4O4)1.5(C2H6OS)]·0.67C2H6OS·0.25C4H4N2 |
Mr | 704.26 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 223 |
a, b, c (Å) | 11.1722 (5), 24.8188 (11), 13.9443 (6) |
β (°) | 97.968 (1) |
V (Å3) | 3829.2 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.80 |
Crystal size (mm) | 0.48 × 0.47 × 0.38 |
Data collection | |
Diffractometer | Bruker APEX area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.626, 0.752 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 43211, 8752, 7451 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.181, 1.05 |
No. of reflections | 8752 |
No. of parameters | 427 |
No. of restraints | 105 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.44, −0.61 |
Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001) and OLEX (Dolomanov et al., 2003), publCIF (Westrip, 2007).
Zn1—O1 | 1.959 (2) | Zn1—O3i | 1.993 (2) |
Zn1—O5 | 1.972 (2) | Zn1—O7 | 2.047 (2) |
Symmetry code: (i) x+1/2, −y+3/2, z−1/2. |
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Dimethyl sulfoxide (DMSO) occassionally gets trapped in organic molecular crystals through multi-point recognition between the solvent and molecule (Nangia & Desiraju, 1999). Similarly, coordination polymers synthesized using DMSO as solvent sometimes intercalate DMSO as solvated molecule (Wang et al., 2001, Yang et al., 2005). Our attempt to synthesize porous coordination polymers with the zinc ion, terephthalate dianion and pyrazine in DMSO resulted in the formation of the title compound, (I).
The zinc atom exists in a tetrahedral geometry (Table 1), being coordinated to one oxygen atom from a DMSO moleucle and three oxygen atoms from three different terephthalate anions (Fig. 1). The manner of bridging generates a wavy, honeycomb polyanionic layer (Figure 2). The space between adjacent layers is occupied by the bulky cation as well as the DMSO and pyrazine solvent molecules. The guest cations and molecules take up more than 60% of the unit cell volume. These guests interact with the layers through weak van der Waals interactions.