The structure of the title molecule, C
32H
30N
2O
4S
2, is stabilized by N—H
O, N—H
S, C—H
S and C—H
O hydrogen bonds. The molecular packing in the crystal is stabilized by intermolecular C—H
O and C—H
π interactions.
Supporting information
CCDC reference: 222864
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.050
- wR factor = 0.142
- Data-to-parameter ratio = 17.6
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ..... 0.99
Alert level C
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of 31.00 A 3
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 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
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
In high dilution condition, benzene-1,2-dioxy-bis(ethanoylchloride) (1 mmol) and 1,2-dimethyl-4,5-bis[mercaptomethyl(2-aminophenyl)]benzene (1 mmol) were cyclized in chloroform in the presence of triethylamine to afford the title compound. The compound was recrystallized from chloroform/hexane (1:1) mixture by slow evaporation method.
H atoms were positioned geometrically and were treated as riding on their parent atoms with aromatic C—H distance of 0.93 Å, methyl C—H distance of 0.96 Å, methylene C—H distance of 0.97 Å and N—H distance of 0.86 Å. The Uiso(H) = 1.5Ueq(C) for the methyl H and 1.2Ueq(C or N) for other H atoms. A rotating group model was used for the methyl groups. Reflections were measured to θmax = 28.02° with 92% completeness, but the data are 99% complete to 25°.
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: 'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 1990)'; software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
34,35-Dimethyl-13,20-dioxa-10,23-diaza-3,30- dithiapentacyclo[30.4.0.0
4,9.0
14,19.0
24,29]hexatriconta- 1(36),4,6,8,14,16,18,24,26,28,32,34-dodecane-11,22-dione
top
Crystal data top
C32H30N2O4S2 | Z = 2 |
Mr = 570.70 | F(000) = 600 |
Triclinic, P1 | Dx = 1.314 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.5860 (7) Å | Cell parameters from 2732 reflections |
b = 12.909 (1) Å | θ = 2.7–26.3° |
c = 14.7552 (11) Å | µ = 0.23 mm−1 |
α = 65.065 (1)° | T = 293 K |
β = 84.701 (1)° | Needle, colourless |
γ = 76.522 (1)° | 0.25 × 0.19 × 0.14 mm |
V = 1442.1 (2) Å3 | |
Data collection top
CCD Area Detector diffractometer | 4720 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.017 |
Graphite monochromator | θmax = 28.0°, θmin = 1.5° |
ω scans | h = −10→11 |
9187 measured reflections | k = −17→13 |
6389 independent reflections | l = −19→18 |
Refinement top
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0775P)2 + 0.1322P] where P = (Fo2 + 2Fc2)/3 |
6389 reflections | (Δ/σ)max < 0.001 |
363 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
Crystal data top
C32H30N2O4S2 | γ = 76.522 (1)° |
Mr = 570.70 | V = 1442.1 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.5860 (7) Å | Mo Kα radiation |
b = 12.909 (1) Å | µ = 0.23 mm−1 |
c = 14.7552 (11) Å | T = 293 K |
α = 65.065 (1)° | 0.25 × 0.19 × 0.14 mm |
β = 84.701 (1)° | |
Data collection top
CCD Area Detector diffractometer | 4720 reflections with I > 2σ(I) |
9187 measured reflections | Rint = 0.017 |
6389 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.27 e Å−3 |
6389 reflections | Δρmin = −0.19 e Å−3 |
363 parameters | |
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. |
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 (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.60471 (6) | 0.67242 (5) | 0.02648 (4) | 0.05294 (17) | |
S2 | 0.08240 (6) | 0.93075 (5) | 0.13042 (4) | 0.05350 (17) | |
C1 | 0.4526 (2) | 0.78974 (19) | 0.03959 (16) | 0.0467 (5) | |
H1A | 0.4292 | 0.8538 | −0.0258 | 0.056* | |
H1B | 0.3551 | 0.7615 | 0.0643 | 0.056* | |
C2 | 0.5013 (2) | 0.83511 (16) | 0.10914 (14) | 0.0392 (4) | |
C3 | 0.6357 (2) | 0.77888 (17) | 0.17014 (15) | 0.0416 (4) | |
H3 | 0.7012 | 0.7131 | 0.1652 | 0.050* | |
C4 | 0.6772 (2) | 0.81622 (17) | 0.23832 (15) | 0.0433 (5) | |
C5 | 0.5842 (3) | 0.91729 (19) | 0.24357 (16) | 0.0485 (5) | |
C6 | 0.4517 (2) | 0.97501 (17) | 0.18100 (16) | 0.0466 (5) | |
H6 | 0.3905 | 1.0438 | 0.1829 | 0.056* | |
C7 | 0.4055 (2) | 0.93539 (16) | 0.11571 (14) | 0.0414 (4) | |
C8 | 0.2493 (2) | 0.99691 (18) | 0.06072 (15) | 0.0483 (5) | |
H8A | 0.2577 | 0.9936 | −0.0040 | 0.058* | |
H8B | 0.2271 | 1.0786 | 0.0497 | 0.058* | |
C9 | 0.0967 (3) | 0.95085 (19) | 0.24072 (17) | 0.0507 (5) | |
C10 | 0.0263 (3) | 1.0583 (2) | 0.2429 (2) | 0.0695 (7) | |
H10 | −0.0344 | 1.1160 | 0.1883 | 0.083* | |
C11 | 0.0441 (4) | 1.0810 (3) | 0.3230 (3) | 0.0855 (9) | |
H11 | −0.0025 | 1.1539 | 0.3226 | 0.103* | |
C12 | 0.1312 (4) | 0.9956 (3) | 0.4042 (2) | 0.0824 (9) | |
H12 | 0.1442 | 1.0114 | 0.4587 | 0.099* | |
C13 | 0.2001 (3) | 0.8863 (2) | 0.40665 (19) | 0.0662 (7) | |
H13 | 0.2568 | 0.8287 | 0.4630 | 0.079* | |
C14 | 0.1844 (3) | 0.86299 (18) | 0.32448 (16) | 0.0491 (5) | |
N15 | 0.2544 (2) | 0.75511 (14) | 0.32130 (12) | 0.0475 (4) | |
H15 | 0.2183 | 0.7426 | 0.2752 | 0.057* | |
C16 | 0.3702 (3) | 0.66797 (18) | 0.37988 (15) | 0.0508 (5) | |
O17 | 0.4287 (3) | 0.66545 (15) | 0.45288 (13) | 0.0820 (6) | |
C18 | 0.4319 (3) | 0.57131 (18) | 0.34594 (16) | 0.0497 (5) | |
H18A | 0.5376 | 0.5780 | 0.3178 | 0.060* | |
H18B | 0.4431 | 0.4970 | 0.4038 | 0.060* | |
O19 | 0.33351 (17) | 0.57054 (12) | 0.27396 (10) | 0.0470 (3) | |
C20 | 0.2054 (2) | 0.51742 (16) | 0.30795 (14) | 0.0413 (4) | |
C21 | 0.1652 (3) | 0.4608 (2) | 0.40622 (16) | 0.0557 (6) | |
H21 | 0.2265 | 0.4572 | 0.4566 | 0.067* | |
C22 | 0.0342 (3) | 0.4091 (2) | 0.43072 (17) | 0.0627 (6) | |
H22 | 0.0089 | 0.3701 | 0.4975 | 0.075* | |
C23 | −0.0582 (3) | 0.4149 (2) | 0.35747 (17) | 0.0575 (6) | |
H23 | −0.1463 | 0.3802 | 0.3744 | 0.069* | |
C24 | −0.0203 (3) | 0.47248 (19) | 0.25805 (16) | 0.0505 (5) | |
H24 | −0.0839 | 0.4775 | 0.2080 | 0.061* | |
C25 | 0.1114 (2) | 0.52226 (17) | 0.23332 (14) | 0.0412 (4) | |
O26 | 0.16260 (17) | 0.57847 (13) | 0.13746 (10) | 0.0507 (4) | |
C27 | 0.0718 (3) | 0.5832 (2) | 0.05983 (15) | 0.0510 (5) | |
H27A | −0.0320 | 0.6351 | 0.0550 | 0.061* | |
H27B | 0.0546 | 0.5059 | 0.0754 | 0.061* | |
C28 | 0.1565 (2) | 0.62643 (17) | −0.03845 (14) | 0.0421 (4) | |
O29 | 0.08272 (18) | 0.65581 (14) | −0.11488 (10) | 0.0581 (4) | |
N30 | 0.3118 (2) | 0.62704 (15) | −0.03374 (12) | 0.0455 (4) | |
H30 | 0.3507 | 0.6022 | 0.0252 | 0.055* | |
C31 | 0.4183 (2) | 0.66316 (17) | −0.11314 (15) | 0.0436 (5) | |
C32 | 0.3918 (3) | 0.6734 (2) | −0.20816 (16) | 0.0547 (6) | |
H32 | 0.2979 | 0.6583 | −0.2219 | 0.066* | |
C33 | 0.5030 (3) | 0.7056 (2) | −0.28215 (18) | 0.0617 (6) | |
H33 | 0.4835 | 0.7123 | −0.3456 | 0.074* | |
C34 | 0.6425 (3) | 0.7278 (2) | −0.26367 (19) | 0.0618 (6) | |
H34 | 0.7173 | 0.7490 | −0.3142 | 0.074* | |
C35 | 0.6718 (3) | 0.71883 (19) | −0.17000 (18) | 0.0548 (6) | |
H35 | 0.7665 | 0.7339 | −0.1575 | 0.066* | |
C36 | 0.5596 (2) | 0.68718 (17) | −0.09389 (16) | 0.0451 (5) | |
C37 | 0.8168 (3) | 0.7444 (2) | 0.30775 (18) | 0.0604 (6) | |
H37A | 0.8817 | 0.7948 | 0.3096 | 0.091* | |
H37B | 0.8797 | 0.6887 | 0.2844 | 0.091* | |
H37C | 0.7782 | 0.7038 | 0.3737 | 0.091* | |
C38 | 0.6196 (3) | 0.9619 (3) | 0.3170 (2) | 0.0765 (8) | |
H38A | 0.5424 | 1.0324 | 0.3087 | 0.115* | |
H38B | 0.7251 | 0.9779 | 0.3053 | 0.115* | |
H38C | 0.6137 | 0.9039 | 0.3838 | 0.115* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0410 (3) | 0.0567 (3) | 0.0654 (4) | 0.0006 (2) | −0.0130 (3) | −0.0324 (3) |
S2 | 0.0388 (3) | 0.0532 (3) | 0.0536 (3) | −0.0059 (2) | −0.0082 (2) | −0.0082 (3) |
C1 | 0.0381 (11) | 0.0512 (12) | 0.0489 (12) | −0.0037 (9) | −0.0033 (9) | −0.0213 (10) |
C2 | 0.0362 (10) | 0.0388 (10) | 0.0390 (10) | −0.0115 (8) | 0.0018 (8) | −0.0111 (8) |
C3 | 0.0360 (10) | 0.0376 (10) | 0.0466 (11) | −0.0053 (8) | −0.0009 (8) | −0.0141 (9) |
C4 | 0.0362 (10) | 0.0445 (11) | 0.0454 (11) | −0.0109 (8) | −0.0020 (9) | −0.0135 (9) |
C5 | 0.0451 (12) | 0.0497 (12) | 0.0548 (12) | −0.0153 (9) | 0.0020 (10) | −0.0232 (10) |
C6 | 0.0434 (11) | 0.0368 (11) | 0.0571 (12) | −0.0077 (9) | 0.0024 (10) | −0.0179 (9) |
C7 | 0.0373 (10) | 0.0362 (10) | 0.0414 (10) | −0.0085 (8) | 0.0014 (8) | −0.0071 (8) |
C8 | 0.0440 (11) | 0.0403 (11) | 0.0448 (11) | −0.0021 (9) | −0.0034 (9) | −0.0054 (9) |
C9 | 0.0421 (11) | 0.0439 (12) | 0.0560 (13) | −0.0093 (9) | 0.0073 (10) | −0.0125 (10) |
C10 | 0.0582 (15) | 0.0526 (15) | 0.0838 (19) | −0.0042 (11) | 0.0164 (13) | −0.0222 (14) |
C11 | 0.088 (2) | 0.0618 (18) | 0.108 (3) | −0.0139 (16) | 0.0322 (19) | −0.0442 (19) |
C12 | 0.097 (2) | 0.086 (2) | 0.087 (2) | −0.0350 (18) | 0.0329 (18) | −0.0551 (19) |
C13 | 0.0782 (18) | 0.0689 (17) | 0.0557 (14) | −0.0253 (14) | 0.0100 (13) | −0.0267 (13) |
C14 | 0.0492 (12) | 0.0468 (12) | 0.0499 (12) | −0.0171 (9) | 0.0084 (10) | −0.0168 (10) |
N15 | 0.0551 (11) | 0.0420 (10) | 0.0431 (9) | −0.0107 (8) | −0.0110 (8) | −0.0132 (8) |
C16 | 0.0629 (14) | 0.0413 (11) | 0.0402 (11) | −0.0156 (10) | −0.0157 (10) | −0.0038 (9) |
O17 | 0.1222 (16) | 0.0571 (11) | 0.0632 (11) | −0.0074 (10) | −0.0494 (11) | −0.0179 (9) |
C18 | 0.0501 (12) | 0.0427 (12) | 0.0473 (12) | −0.0103 (9) | −0.0162 (10) | −0.0066 (9) |
O19 | 0.0533 (9) | 0.0450 (8) | 0.0407 (7) | −0.0150 (6) | −0.0087 (6) | −0.0117 (6) |
C20 | 0.0462 (11) | 0.0347 (10) | 0.0409 (10) | −0.0074 (8) | −0.0004 (9) | −0.0142 (8) |
C21 | 0.0666 (15) | 0.0595 (14) | 0.0411 (12) | −0.0201 (11) | −0.0045 (11) | −0.0164 (10) |
C22 | 0.0765 (17) | 0.0683 (16) | 0.0414 (12) | −0.0282 (13) | 0.0075 (12) | −0.0157 (11) |
C23 | 0.0606 (14) | 0.0642 (15) | 0.0531 (13) | −0.0273 (12) | 0.0108 (11) | −0.0241 (11) |
C24 | 0.0506 (12) | 0.0599 (14) | 0.0473 (12) | −0.0202 (10) | 0.0042 (10) | −0.0247 (10) |
C25 | 0.0465 (11) | 0.0393 (10) | 0.0373 (10) | −0.0089 (8) | 0.0017 (8) | −0.0158 (8) |
O26 | 0.0545 (9) | 0.0641 (10) | 0.0377 (7) | −0.0268 (7) | −0.0012 (6) | −0.0176 (7) |
C27 | 0.0477 (12) | 0.0649 (14) | 0.0419 (11) | −0.0217 (10) | −0.0052 (9) | −0.0176 (10) |
C28 | 0.0457 (11) | 0.0408 (11) | 0.0400 (10) | −0.0138 (8) | −0.0041 (9) | −0.0137 (9) |
O29 | 0.0532 (9) | 0.0775 (11) | 0.0411 (8) | −0.0230 (8) | −0.0085 (7) | −0.0157 (8) |
N30 | 0.0453 (10) | 0.0541 (10) | 0.0372 (9) | −0.0156 (8) | −0.0056 (7) | −0.0152 (8) |
C31 | 0.0447 (11) | 0.0422 (11) | 0.0437 (11) | −0.0086 (9) | −0.0003 (9) | −0.0180 (9) |
C32 | 0.0581 (14) | 0.0620 (14) | 0.0491 (12) | −0.0169 (11) | −0.0002 (11) | −0.0256 (11) |
C33 | 0.0703 (16) | 0.0642 (15) | 0.0516 (13) | −0.0118 (12) | 0.0069 (12) | −0.0277 (12) |
C34 | 0.0617 (15) | 0.0554 (14) | 0.0653 (15) | −0.0115 (11) | 0.0222 (12) | −0.0270 (12) |
C35 | 0.0412 (12) | 0.0529 (13) | 0.0733 (16) | −0.0083 (10) | 0.0086 (11) | −0.0314 (12) |
C36 | 0.0399 (11) | 0.0405 (11) | 0.0561 (12) | −0.0031 (8) | −0.0021 (9) | −0.0235 (10) |
C37 | 0.0536 (14) | 0.0612 (15) | 0.0646 (15) | −0.0058 (11) | −0.0181 (12) | −0.0240 (12) |
C38 | 0.0702 (18) | 0.0828 (19) | 0.096 (2) | −0.0105 (14) | −0.0125 (15) | −0.0563 (17) |
Geometric parameters (Å, º) top
S1—C36 | 1.774 (2) | C18—H18B | 0.97 |
S1—C1 | 1.821 (2) | O19—C20 | 1.376 (2) |
S2—C9 | 1.772 (2) | C20—C21 | 1.374 (3) |
S2—C8 | 1.844 (2) | C20—C25 | 1.396 (3) |
C1—C2 | 1.507 (3) | C21—C22 | 1.383 (3) |
C1—H1A | 0.97 | C21—H21 | 0.93 |
C1—H1B | 0.97 | C22—C23 | 1.365 (3) |
C2—C3 | 1.385 (3) | C22—H22 | 0.93 |
C2—C7 | 1.399 (3) | C23—C24 | 1.384 (3) |
C3—C4 | 1.388 (3) | C23—H23 | 0.93 |
C3—H3 | 0.93 | C24—C25 | 1.375 (3) |
C4—C5 | 1.391 (3) | C24—H24 | 0.93 |
C4—C37 | 1.501 (3) | C25—O26 | 1.374 (2) |
C5—C6 | 1.386 (3) | O26—C27 | 1.416 (2) |
C5—C38 | 1.506 (3) | C27—C28 | 1.502 (3) |
C6—C7 | 1.388 (3) | C27—H27A | 0.97 |
C6—H6 | 0.93 | C27—H27B | 0.97 |
C7—C8 | 1.500 (3) | C28—O29 | 1.215 (2) |
C8—H8A | 0.97 | C28—N30 | 1.343 (2) |
C8—H8B | 0.97 | N30—C31 | 1.402 (3) |
C9—C10 | 1.391 (3) | N30—H30 | 0.86 |
C9—C14 | 1.405 (3) | C31—C32 | 1.387 (3) |
C10—C11 | 1.361 (4) | C31—C36 | 1.401 (3) |
C10—H10 | 0.93 | C32—C33 | 1.374 (3) |
C11—C12 | 1.370 (4) | C32—H32 | 0.93 |
C11—H11 | 0.93 | C33—C34 | 1.370 (3) |
C12—C13 | 1.383 (4) | C33—H33 | 0.93 |
C12—H12 | 0.93 | C34—C35 | 1.379 (3) |
C13—C14 | 1.391 (3) | C34—H34 | 0.93 |
C13—H13 | 0.93 | C35—C36 | 1.397 (3) |
C14—N15 | 1.401 (3) | C35—H35 | 0.93 |
N15—C16 | 1.348 (3) | C37—H37A | 0.96 |
N15—H15 | 0.86 | C37—H37B | 0.96 |
C16—O17 | 1.215 (2) | C37—H37C | 0.96 |
C16—C18 | 1.503 (3) | C38—H38A | 0.96 |
C18—O19 | 1.421 (2) | C38—H38B | 0.96 |
C18—H18A | 0.97 | C38—H38C | 0.96 |
| | | |
C36—S1—C1 | 101.71 (9) | C20—O19—C18 | 117.9 (2) |
C9—S2—C8 | 98.60 (10) | O19—C20—C21 | 126.10 (18) |
C2—C1—S1 | 113.54 (14) | O19—C20—C25 | 114.99 (16) |
C2—C1—H1A | 108.9 | C21—C20—C25 | 118.90 (19) |
S1—C1—H1A | 108.9 | C20—C21—C22 | 120.5 (2) |
C2—C1—H1B | 108.9 | C20—C21—H21 | 119.8 |
S1—C1—H1B | 108.9 | C22—C21—H21 | 119.8 |
H1A—C1—H1B | 107.7 | C23—C22—C21 | 120.4 (2) |
C3—C2—C7 | 118.03 (18) | C23—C22—H22 | 119.8 |
C3—C2—C1 | 122.4 (2) | C21—C22—H22 | 119.8 |
C7—C2—C1 | 119.5 (2) | C22—C23—C24 | 119.9 (2) |
C2—C3—C4 | 123.03 (19) | C22—C23—H23 | 120.1 |
C2—C3—H3 | 118.5 | C24—C23—H23 | 120.1 |
C4—C3—H3 | 118.5 | C25—C24—C23 | 119.9 (2) |
C3—C4—C5 | 119.08 (18) | C25—C24—H24 | 120.0 |
C3—C4—C37 | 119.6 (2) | C23—C24—H24 | 120.0 |
C5—C4—C37 | 121.3 (2) | O26—C25—C24 | 124.8 (2) |
C6—C5—C4 | 117.88 (19) | O26—C25—C20 | 114.8 (2) |
C6—C5—C38 | 119.9 (2) | C24—C25—C20 | 120.36 (18) |
C4—C5—C38 | 122.2 (2) | C25—O26—C27 | 116.4 (2) |
C5—C6—C7 | 123.33 (19) | O26—C27—C28 | 110.88 (16) |
C5—C6—H6 | 118.3 | O26—C27—H27A | 109.5 |
C7—C6—H6 | 118.3 | C28—C27—H27A | 109.5 |
C6—C7—C2 | 118.57 (18) | O26—C27—H27B | 109.5 |
C6—C7—C8 | 118.54 (19) | C28—C27—H27B | 109.5 |
C2—C7—C8 | 122.75 (18) | H27A—C27—H27B | 108.1 |
C7—C8—S2 | 111.82 (13) | O29—C28—N30 | 125.13 (19) |
C7—C8—H8A | 109.3 | O29—C28—C27 | 118.83 (18) |
S2—C8—H8A | 109.3 | N30—C28—C27 | 116.03 (17) |
C7—C8—H8B | 109.3 | C28—N30—C31 | 128.0 (2) |
S2—C8—H8B | 109.3 | C28—N30—H30 | 116.0 |
H8A—C8—H8B | 107.9 | C31—N30—H30 | 116.0 |
C10—C9—C14 | 118.9 (2) | C32—C31—C36 | 119.0 (2) |
C10—C9—S2 | 119.3 (2) | C32—C31—N30 | 123.18 (19) |
C14—C9—S2 | 121.7 (2) | C36—C31—N30 | 117.76 (18) |
C11—C10—C9 | 121.5 (3) | C33—C32—C31 | 120.5 (2) |
C11—C10—H10 | 119.2 | C33—C32—H32 | 119.7 |
C9—C10—H10 | 119.2 | C31—C32—H32 | 119.7 |
C10—C11—C12 | 119.4 (3) | C34—C33—C32 | 120.8 (2) |
C10—C11—H11 | 120.3 | C34—C33—H33 | 119.6 |
C12—C11—H11 | 120.3 | C32—C33—H33 | 119.6 |
C11—C12—C13 | 121.2 (3) | C33—C34—C35 | 119.9 (2) |
C11—C12—H12 | 119.4 | C33—C34—H34 | 120.0 |
C13—C12—H12 | 119.4 | C35—C34—H34 | 120.0 |
C12—C13—C14 | 119.7 (3) | C34—C35—C36 | 120.2 (2) |
C12—C13—H13 | 120.2 | C34—C35—H35 | 119.9 |
C14—C13—H13 | 120.2 | C36—C35—H35 | 119.9 |
C13—C14—N15 | 122.5 (2) | C31—C36—C35 | 119.5 (2) |
C13—C14—C9 | 119.2 (2) | C31—C36—S1 | 121.7 (2) |
N15—C14—C9 | 118.32 (19) | C35—C36—S1 | 118.7 (2) |
C16—N15—C14 | 129.5 (2) | C4—C37—H37A | 109.5 |
C16—N15—H15 | 115.2 | C4—C37—H37B | 109.5 |
C14—N15—H15 | 115.2 | H37A—C37—H37B | 109.5 |
O17—C16—N15 | 125.2 (2) | C4—C37—H37C | 109.5 |
O17—C16—C18 | 120.0 (2) | H37A—C37—H37C | 109.5 |
N15—C16—C18 | 114.76 (17) | H37B—C37—H37C | 109.5 |
O19—C18—C16 | 114.60 (17) | C5—C38—H38A | 109.5 |
O19—C18—H18A | 108.6 | C5—C38—H38B | 109.5 |
C16—C18—H18A | 108.6 | H38A—C38—H38B | 109.5 |
O19—C18—H18B | 108.6 | C5—C38—H38C | 109.5 |
C16—C18—H18B | 108.6 | H38A—C38—H38C | 109.5 |
H18A—C18—H18B | 107.6 | H38B—C38—H38C | 109.5 |
| | | |
C36—S1—C1—C2 | −153.7 (2) | O17—C16—C18—O19 | 167.3 (2) |
S1—C1—C2—C3 | −10.8 (2) | N15—C16—C18—O19 | −15.3 (3) |
S1—C1—C2—C7 | 171.40 (14) | C16—C18—O19—C20 | −83.4 (2) |
C7—C2—C3—C4 | 1.3 (3) | C18—O19—C20—C21 | −2.3 (3) |
C1—C2—C3—C4 | −176.49 (18) | C18—O19—C20—C25 | 178.49 (17) |
C2—C3—C4—C5 | −2.7 (3) | O19—C20—C21—C22 | −178.9 (2) |
C2—C3—C4—C37 | 174.7 (2) | C25—C20—C21—C22 | 0.3 (3) |
C3—C4—C5—C6 | 1.2 (3) | C20—C21—C22—C23 | −0.8 (4) |
C37—C4—C5—C6 | −176.2 (2) | C21—C22—C23—C24 | 0.3 (4) |
C3—C4—C5—C38 | 178.7 (2) | C22—C23—C24—C25 | 0.9 (4) |
C37—C4—C5—C38 | 1.3 (3) | C23—C24—C25—O26 | 178.1 (2) |
C4—C5—C6—C7 | 1.7 (3) | C23—C24—C25—C20 | −1.5 (3) |
C38—C5—C6—C7 | −175.9 (2) | O19—C20—C25—O26 | 0.6 (3) |
C5—C6—C7—C2 | −3.0 (3) | C21—C20—C25—O26 | −178.70 (19) |
C5—C6—C7—C8 | 172.74 (18) | O19—C20—C25—C24 | −179.83 (18) |
C3—C2—C7—C6 | 1.5 (3) | C21—C20—C25—C24 | 0.9 (3) |
C1—C2—C7—C6 | 179.34 (17) | C24—C25—O26—C27 | −0.7 (3) |
C3—C2—C7—C8 | −174.08 (17) | C20—C25—O26—C27 | 178.91 (18) |
C1—C2—C7—C8 | 3.8 (3) | C25—O26—C27—C28 | −169.51 (17) |
C6—C7—C8—S2 | −90.7 (2) | O26—C27—C28—O29 | −166.70 (19) |
C2—C7—C8—S2 | 84.9 (2) | O26—C27—C28—N30 | 14.5 (3) |
C9—S2—C8—C7 | 59.5 (2) | O29—C28—N30—C31 | 1.7 (3) |
C8—S2—C9—C10 | 82.52 (19) | C27—C28—N30—C31 | −179.62 (19) |
C8—S2—C9—C14 | −94.14 (18) | C28—N30—C31—C32 | −19.0 (3) |
C14—C9—C10—C11 | 1.8 (4) | C28—N30—C31—C36 | 162.5 (2) |
S2—C9—C10—C11 | −175.0 (2) | C36—C31—C32—C33 | 0.6 (3) |
C9—C10—C11—C12 | −1.0 (4) | N30—C31—C32—C33 | −177.9 (2) |
C10—C11—C12—C13 | −0.6 (4) | C31—C32—C33—C34 | 0.2 (4) |
C11—C12—C13—C14 | 1.5 (4) | C32—C33—C34—C35 | −0.5 (4) |
C12—C13—C14—N15 | 178.5 (2) | C33—C34—C35—C36 | −0.1 (3) |
C12—C13—C14—C9 | −0.8 (3) | C32—C31—C36—C35 | −1.1 (3) |
C10—C9—C14—C13 | −0.8 (3) | N30—C31—C36—C35 | 177.43 (18) |
S2—C9—C14—C13 | 175.84 (17) | C32—C31—C36—S1 | −178.33 (16) |
C10—C9—C14—N15 | 179.91 (19) | N30—C31—C36—S1 | 0.2 (3) |
S2—C9—C14—N15 | −3.4 (3) | C34—C35—C36—C31 | 0.9 (3) |
C13—C14—N15—C16 | −15.4 (3) | C34—C35—C36—S1 | 178.17 (17) |
C9—C14—N15—C16 | 163.8 (2) | C1—S1—C36—C31 | −67.76 (19) |
C14—N15—C16—O17 | 5.2 (4) | C1—S1—C36—C35 | 115.01 (17) |
C14—N15—C16—C18 | −172.03 (19) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N15—H15···S2 | 0.86 | 2.57 | 3.012 (2) | 113 |
N15—H15···O19 | 0.86 | 2.22 | 2.681 (2) | 114 |
N30—H30···S1 | 0.86 | 2.55 | 2.999 (2) | 113 |
N30—H30···O26 | 0.86 | 2.18 | 2.618 (2) | 111 |
C3—H3···S1 | 0.93 | 2.56 | 3.029 (2) | 112 |
C13—H13···O17 | 0.93 | 2.33 | 2.904 (4) | 120 |
C32—H32···O29 | 0.93 | 2.31 | 2.884 (3) | 119 |
C18—H18B···O17i | 0.97 | 2.39 | 3.300 (3) | 157 |
C27—H27B···O29ii | 0.97 | 2.47 | 3.398 (3) | 161 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z. |
Experimental details
Crystal data |
Chemical formula | C32H30N2O4S2 |
Mr | 570.70 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 8.5860 (7), 12.909 (1), 14.7552 (11) |
α, β, γ (°) | 65.065 (1), 84.701 (1), 76.522 (1) |
V (Å3) | 1442.1 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.25 × 0.19 × 0.14 |
|
Data collection |
Diffractometer | CCD Area Detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9187, 6389, 4720 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.661 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.142, 1.01 |
No. of reflections | 6389 |
No. of parameters | 363 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.19 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N15—H15···S2 | 0.86 | 2.57 | 3.012 (2) | 113 |
N15—H15···O19 | 0.86 | 2.22 | 2.681 (2) | 114 |
N30—H30···S1 | 0.86 | 2.55 | 2.999 (2) | 113 |
N30—H30···O26 | 0.86 | 2.18 | 2.618 (2) | 111 |
C3—H3···S1 | 0.93 | 2.56 | 3.029 (2) | 112 |
C13—H13···O17 | 0.93 | 2.33 | 2.904 (4) | 120 |
C32—H32···O29 | 0.93 | 2.31 | 2.884 (3) | 119 |
C18—H18B···O17i | 0.97 | 2.39 | 3.300 (3) | 157 |
C27—H27B···O29ii | 0.97 | 2.47 | 3.398 (3) | 161 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z. |
Cyclophanes are cyclic systems, consisting of at least one aromatic moiety, bridged by one or more aliphatic chains (De Ridder et al., 2001). Paracyclophane and other π-electron rich hydrocarbons possessing a cavity forming topology are known to form endohedral π-complexes with silver and other soft metal atoms (Addad et al., 1983; Heirtzler et al., 1995; Faust, 1995). We report here the structure of the title compound, (I), a cyclophane.
The structure of (I) with the atom-numbering scheme is shown in Fig. 1. The S—C distances [S1—C36 = 1.774 (2) Å, S1—C1 = 1.821 (2) Å, S2—C9 = 1.772 (2) Å and S2—C8 = 1.844 (2) Å] are comparable to the mean Cphenyl—S [1.773 (9) Å] or Csp3—S [1.819 (19) Å] distances reported by Allen et al. (1987). The widening of the exocyclic angle C24—C25—O26 [124.8 (2)°] and the resultant narrowing of angle C20—C25—O26 [114.8 (2)°] from 120° may be as a result of the short H24···H27B [2.13 Å] contact. The torsion angles C13—C14—N15—C16 = −15.4 (3)°, C9—C14—N15—C16 = 163.8 (2)°, C36—C31—N30—C28 = 162.5 (2)° and C28—N30—C31—C32 = −19.0 (3)° indicate that both the amide planes are twisted away from the attached phenyl rings; the dihedral angle between the N15/C16/O17/C18 plane and B ring is 13.3 (1)° and that between N30/C28/O29/C27 plane and C ring is 17.2 (1)°. The dihedral angle between the phenyl rings A and D [87.3 (1)°] and B and C [86.4 (1)°] indicate that they are nearly perpendicular to each other.
The molecular structure is stabilized by N—H···O, N—H···S, C—H···S and C—H···O hydrogen bonds. In the crystal structure, C18—H18B···O17i hydrogen bonds link the inversion-related molecules to form dimers (Fig. 2). The dimers are linked together by C27—H27B···O29ii hydrogen bonds (Table. 1). The structure is further stabilized by intermolecular C—H···π interactions involving H37B and ring D of the molecule translated by a unit along the a axis [H37B··· CgD = 2.79 Å, C37···CgD 3.638 (3) Å and C37—H37B···CgD = 148°, where CgD is the centroid of the ring D in the translated molecule].