


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808036003/hb2835sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808036003/hb2835Isup2.hkl |
CCDC reference: 712401
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.006 Å
- R factor = 0.069
- wR factor = 0.219
- Data-to-parameter ratio = 16.0
checkCIF/PLATON results
No syntax errors found
Alert level C Value of measurement temperature given = 296.000 Value of melting point given = 0.000 PLAT083_ALERT_2_C SHELXL Second Parameter in WGHT unusually Large. 7.00 PLAT230_ALERT_2_C Hirshfeld Test Diff for C3 -- C4 .. 6.36 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 -- C5 .. 5.46 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C10 -- C11 .. 6.02 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C16 -- C17 .. 6.39 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C17 -- C18 .. 6.20 su PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT234_ALERT_4_C Large Hirshfeld Difference N1 -- C25 .. 0.10 Ang. PLAT234_ALERT_4_C Large Hirshfeld Difference C15 -- C16 .. 0.11 Ang. PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C9 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C8 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C7 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C21
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 44
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 14 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 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 6 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Propane-1,3-diamine 1.85 g (25 mmol) was dissolved in 2 M sodium hydroxide and the solution was cooled to 0 °C, a solution of 2,4,6-trimethylbenzenesulfonyl chloride 10.9 g (50 mmol) in CH2Cl2 (25 ml) was added dropwise. The reaction mixture was then stirred at room temperture for 18 h. The organic phase was separated from the aqueous phase and washed with 0.5 M HCl solution and brine. The CH2Cl2 layer was dried over sodium sulfate, filtered and the solvent removed in vacuo, and the residue purified by chromatography.
A mixture of N1,N3—Bis(mesitylenesulfonyl)-1,3-propyl-diamine 1.05 g (2.33 mmol) and 60% NaH (5.35 mmol, 0.22 g) in DMF 20 ml was stirred at 0 °C for 0.5 h, then warmed to room temperature for 0.5 h. N-(3-bromopropyl)phthalimide 1.57 g (5.82 mmol) was added and the reaction mixture was stirred at 40 °C for 4 h, then EtoH (2.5 ml) and water (5 ml) were added, the solvent was removed in vacuo at 80 °C, the residue was dissolved in CHCl3 and washed with water, the organic layer was dried over anhydrous sodium sulfate and filtered, then concentrated in vacuo, the residue was purified by chromatography. Colorless rod crystal of (I) were obtained.
The H atoms were positioned geogmetrically (N—H = 0.86 Å, C—H = 0.93–0.97Å) and refined as riding with Uiso(H)=1.2Ueq(carrier) or Uiso(H)=1.5Ueq(methyl-C).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).
C32H39N3O6S2 | F(000) = 2656 |
Mr = 625.78 | Dx = 1.313 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 6528 reflections |
a = 32.042 (3) Å | θ = 2.4–28.1° |
b = 9.9782 (8) Å | µ = 0.22 mm−1 |
c = 25.105 (2) Å | T = 296 K |
β = 127.917 (1)° | Block, colourless |
V = 6332.1 (9) Å3 | 0.18 × 0.15 × 0.13 mm |
Z = 8 |
Bruker SMART CCD diffractometer | 6212 independent reflections |
Radiation source: fine-focus sealed tube | 4574 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ω scans | θmax = 26.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −25→39 |
Tmin = 0.962, Tmax = 0.973 | k = −12→11 |
17128 measured reflections | l = −30→21 |
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)] = 0.069 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.219 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.1169P)2 + 7.2057P] where P = (Fo2 + 2Fc2)/3 |
6212 reflections | (Δ/σ)max < 0.001 |
388 parameters | Δρmax = 0.80 e Å−3 |
44 restraints | Δρmin = −0.57 e Å−3 |
C32H39N3O6S2 | V = 6332.1 (9) Å3 |
Mr = 625.78 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 32.042 (3) Å | µ = 0.22 mm−1 |
b = 9.9782 (8) Å | T = 296 K |
c = 25.105 (2) Å | 0.18 × 0.15 × 0.13 mm |
β = 127.917 (1)° |
Bruker SMART CCD diffractometer | 6212 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | 4574 reflections with I > 2σ(I) |
Tmin = 0.962, Tmax = 0.973 | Rint = 0.022 |
17128 measured reflections |
R[F2 > 2σ(F2)] = 0.069 | 44 restraints |
wR(F2) = 0.219 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.80 e Å−3 |
6212 reflections | Δρmin = −0.57 e Å−3 |
388 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.15326 (3) | 0.47012 (8) | 0.46771 (4) | 0.0531 (3) | |
S2 | 0.06920 (4) | 0.72487 (9) | 0.64731 (6) | 0.0655 (3) | |
C1 | 0.14805 (12) | 0.2922 (3) | 0.45787 (15) | 0.0464 (7) | |
C2 | 0.10216 (14) | 0.2310 (3) | 0.40203 (16) | 0.0539 (8) | |
C3 | 0.10074 (16) | 0.0918 (4) | 0.39911 (18) | 0.0635 (9) | |
H3A | 0.0703 | 0.0502 | 0.3626 | 0.076* | |
C4 | 0.1424 (2) | 0.0131 (4) | 0.4479 (2) | 0.0757 (9) | |
C5 | 0.18654 (16) | 0.0764 (4) | 0.50242 (19) | 0.0637 (9) | |
H5A | 0.2148 | 0.0242 | 0.5361 | 0.076* | |
C6 | 0.19082 (13) | 0.2140 (3) | 0.50937 (17) | 0.0546 (8) | |
C7 | 0.24128 (15) | 0.2685 (4) | 0.57208 (19) | 0.0734 (10) | |
H7A | 0.2644 | 0.1956 | 0.5992 | 0.110* | |
H7B | 0.2334 | 0.3194 | 0.5974 | 0.110* | |
H7C | 0.2583 | 0.3253 | 0.5597 | 0.110* | |
C8 | 0.1398 (2) | −0.1383 (4) | 0.4422 (2) | 0.0849 (10) | |
H8A | 0.1062 | −0.1645 | 0.4014 | 0.127* | |
H8B | 0.1439 | −0.1763 | 0.4803 | 0.127* | |
H8C | 0.1676 | −0.1700 | 0.4413 | 0.127* | |
C9 | 0.05315 (15) | 0.3038 (5) | 0.34304 (18) | 0.0761 (11) | |
H9A | 0.0273 | 0.2393 | 0.3114 | 0.114* | |
H9B | 0.0627 | 0.3598 | 0.3210 | 0.114* | |
H9C | 0.0385 | 0.3580 | 0.3595 | 0.114* | |
C10 | 0.10008 (13) | 0.4624 (3) | 0.51695 (17) | 0.0581 (8) | |
H10A | 0.0998 | 0.3656 | 0.5203 | 0.070* | |
H10B | 0.0691 | 0.4888 | 0.4724 | 0.070* | |
C11 | 0.09849 (17) | 0.5273 (4) | 0.5705 (2) | 0.0732 (10) | |
H11A | 0.0740 | 0.4792 | 0.5740 | 0.088* | |
H11B | 0.1333 | 0.5236 | 0.6140 | 0.088* | |
C12 | 0.08133 (16) | 0.6696 (4) | 0.55154 (18) | 0.0698 (10) | |
H12A | 0.0432 | 0.6719 | 0.5171 | 0.084* | |
H12B | 0.0972 | 0.7070 | 0.5321 | 0.084* | |
C13 | 0.05511 (12) | 0.8878 (3) | 0.66060 (17) | 0.0512 (7) | |
C14 | 0.08566 (13) | 0.9494 (4) | 0.72467 (17) | 0.0554 (8) | |
C15 | 0.07141 (15) | 1.0790 (4) | 0.7284 (2) | 0.0718 (10) | |
H15A | 0.0910 | 1.1211 | 0.7702 | 0.086* | |
C16 | 0.03042 (19) | 1.1470 (5) | 0.6740 (3) | 0.1001 (12) | |
C17 | 0.00179 (16) | 1.0841 (4) | 0.6122 (2) | 0.0822 (12) | |
H17A | −0.0259 | 1.1306 | 0.5745 | 0.099* | |
C18 | 0.01232 (15) | 0.9547 (5) | 0.6035 (2) | 0.0743 (9) | |
C19 | −0.02361 (16) | 0.8980 (5) | 0.5329 (2) | 0.0848 (10) | |
H19A | −0.0494 | 0.9641 | 0.5028 | 0.127* | |
H19B | −0.0413 | 0.8201 | 0.5326 | 0.127* | |
H19C | −0.0030 | 0.8737 | 0.5185 | 0.127* | |
C20 | 0.0171 (2) | 1.2887 (5) | 0.6807 (3) | 0.1087 (13) | |
H20A | 0.0404 | 1.3153 | 0.7273 | 0.163* | |
H20B | −0.0188 | 1.2922 | 0.6646 | 0.163* | |
H20C | 0.0215 | 1.3484 | 0.6545 | 0.163* | |
C21 | 0.13243 (15) | 0.8889 (5) | 0.78906 (18) | 0.0743 (11) | |
H21A | 0.1462 | 0.9517 | 0.8253 | 0.111* | |
H21B | 0.1593 | 0.8679 | 0.7844 | 0.111* | |
H21C | 0.1217 | 0.8085 | 0.7987 | 0.111* | |
C22 | 0.14972 (14) | 0.8142 (4) | 0.65501 (19) | 0.0644 (9) | |
H22A | 0.1754 | 0.7424 | 0.6717 | 0.077* | |
H22B | 0.1547 | 0.8552 | 0.6936 | 0.077* | |
C23 | 0.16017 (16) | 0.9152 (4) | 0.62171 (19) | 0.0692 (10) | |
H23A | 0.1295 | 0.9732 | 0.5946 | 0.083* | |
H23B | 0.1647 | 0.8699 | 0.5914 | 0.083* | |
C24 | 0.20845 (15) | 1.0008 (4) | 0.67022 (18) | 0.0644 (9) | |
H24A | 0.2389 | 0.9430 | 0.6991 | 0.077* | |
H24B | 0.2152 | 1.0570 | 0.6447 | 0.077* | |
C25 | 0.16924 (18) | 1.1983 (4) | 0.68724 (19) | 0.0795 (9) | |
C26 | 0.17520 (14) | 1.2568 (3) | 0.74571 (17) | 0.0596 (8) | |
C27 | 0.15189 (16) | 1.3666 (4) | 0.7500 (2) | 0.0748 (11) | |
H27A | 0.1280 | 1.4190 | 0.7123 | 0.090* | |
C28 | 0.16498 (18) | 1.3968 (4) | 0.8121 (2) | 0.0789 (11) | |
H28A | 0.1497 | 1.4712 | 0.8162 | 0.095* | |
C29 | 0.20005 (17) | 1.3201 (4) | 0.8680 (2) | 0.0719 (10) | |
H29A | 0.2080 | 1.3429 | 0.9093 | 0.086* | |
C30 | 0.22369 (14) | 1.2090 (4) | 0.86355 (18) | 0.0636 (9) | |
H30A | 0.2474 | 1.1565 | 0.9013 | 0.076* | |
C31 | 0.21105 (12) | 1.1789 (3) | 0.80191 (16) | 0.0528 (7) | |
C32 | 0.22889 (12) | 1.0682 (3) | 0.78088 (16) | 0.0522 (7) | |
O1 | 0.20542 (11) | 0.5116 (3) | 0.49361 (14) | 0.0727 (7) | |
O2 | 0.11048 (11) | 0.5309 (3) | 0.40790 (13) | 0.0741 (7) | |
O3 | 0.10576 (13) | 0.6647 (3) | 0.71039 (18) | 0.0900 (9) | |
O4 | 0.14220 (13) | 1.2330 (3) | 0.62932 (13) | 0.0890 (8) | |
O5 | 0.26026 (10) | 0.9802 (3) | 0.81456 (12) | 0.0691 (7) | |
O6 | 0.02164 (12) | 0.6529 (3) | 0.59969 (18) | 0.0939 (10) | |
N1 | 0.20210 (11) | 1.0851 (3) | 0.71198 (13) | 0.0566 (7) | |
N2 | 0.09614 (12) | 0.7566 (3) | 0.61035 (16) | 0.0662 (8) | |
N3 | 0.14813 (10) | 0.5046 (3) | 0.52664 (13) | 0.0523 (6) | |
H3B | 0.1729 | 0.5466 | 0.5626 | 0.063* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0687 (5) | 0.0447 (4) | 0.0570 (5) | 0.0021 (4) | 0.0443 (4) | 0.0024 (3) |
S2 | 0.0762 (6) | 0.0477 (5) | 0.0974 (7) | −0.0042 (4) | 0.0659 (6) | −0.0118 (5) |
C1 | 0.0573 (17) | 0.0451 (15) | 0.0488 (16) | 0.0052 (13) | 0.0387 (15) | 0.0006 (13) |
C2 | 0.0663 (19) | 0.0585 (19) | 0.0489 (16) | 0.0028 (15) | 0.0414 (16) | −0.0046 (14) |
C3 | 0.082 (2) | 0.061 (2) | 0.0574 (19) | −0.0106 (18) | 0.0483 (19) | −0.0156 (16) |
C4 | 0.127 (3) | 0.0491 (15) | 0.094 (2) | 0.0034 (17) | 0.089 (2) | −0.0075 (15) |
C5 | 0.085 (2) | 0.0552 (19) | 0.068 (2) | 0.0204 (18) | 0.056 (2) | 0.0112 (17) |
C6 | 0.0643 (19) | 0.0556 (18) | 0.0589 (18) | 0.0071 (15) | 0.0454 (17) | 0.0024 (15) |
C7 | 0.060 (2) | 0.078 (3) | 0.062 (2) | 0.0080 (19) | 0.0281 (18) | 0.0070 (19) |
C8 | 0.131 (3) | 0.0509 (15) | 0.098 (2) | 0.0032 (17) | 0.083 (2) | −0.0078 (15) |
C9 | 0.064 (2) | 0.090 (3) | 0.054 (2) | 0.005 (2) | 0.0263 (18) | −0.0025 (19) |
C10 | 0.0620 (19) | 0.0545 (18) | 0.0641 (19) | −0.0097 (15) | 0.0420 (17) | −0.0172 (15) |
C11 | 0.079 (2) | 0.067 (2) | 0.087 (3) | −0.0039 (19) | 0.058 (2) | −0.010 (2) |
C12 | 0.069 (2) | 0.076 (2) | 0.065 (2) | 0.0016 (19) | 0.0412 (19) | −0.0101 (16) |
C13 | 0.0510 (16) | 0.0481 (16) | 0.0657 (19) | 0.0003 (13) | 0.0415 (16) | −0.0056 (14) |
C14 | 0.0531 (17) | 0.062 (2) | 0.0628 (19) | 0.0002 (15) | 0.0417 (16) | −0.0057 (16) |
C15 | 0.067 (2) | 0.069 (2) | 0.089 (3) | −0.0076 (18) | 0.053 (2) | −0.029 (2) |
C16 | 0.083 (2) | 0.068 (2) | 0.151 (3) | 0.0135 (17) | 0.073 (2) | −0.015 (2) |
C17 | 0.061 (2) | 0.074 (2) | 0.098 (3) | 0.0204 (19) | 0.042 (2) | 0.009 (2) |
C18 | 0.0549 (15) | 0.093 (2) | 0.0681 (17) | 0.0012 (15) | 0.0343 (14) | −0.0060 (16) |
C19 | 0.0613 (16) | 0.097 (2) | 0.0718 (17) | 0.0007 (15) | 0.0288 (14) | −0.0062 (16) |
C20 | 0.088 (2) | 0.070 (2) | 0.155 (3) | 0.0145 (17) | 0.069 (2) | −0.015 (2) |
C21 | 0.070 (2) | 0.099 (3) | 0.059 (2) | 0.007 (2) | 0.0428 (19) | 0.004 (2) |
C22 | 0.065 (2) | 0.062 (2) | 0.077 (2) | 0.0052 (17) | 0.0488 (19) | −0.0013 (18) |
C23 | 0.079 (2) | 0.071 (2) | 0.069 (2) | −0.0127 (19) | 0.051 (2) | −0.0134 (18) |
C24 | 0.068 (2) | 0.071 (2) | 0.067 (2) | −0.0084 (18) | 0.0480 (19) | −0.0093 (18) |
C25 | 0.1013 (19) | 0.0670 (16) | 0.0558 (13) | 0.0131 (14) | 0.0410 (14) | 0.0110 (12) |
C26 | 0.0613 (19) | 0.0478 (17) | 0.0597 (19) | −0.0017 (15) | 0.0321 (17) | 0.0019 (14) |
C27 | 0.077 (2) | 0.054 (2) | 0.082 (3) | 0.0068 (18) | 0.043 (2) | 0.0018 (18) |
C28 | 0.094 (3) | 0.051 (2) | 0.108 (3) | 0.002 (2) | 0.070 (3) | −0.009 (2) |
C29 | 0.087 (3) | 0.063 (2) | 0.081 (3) | −0.018 (2) | 0.059 (2) | −0.020 (2) |
C30 | 0.064 (2) | 0.065 (2) | 0.0557 (19) | −0.0042 (17) | 0.0340 (17) | −0.0022 (16) |
C31 | 0.0471 (16) | 0.0491 (17) | 0.0546 (17) | −0.0055 (13) | 0.0274 (14) | −0.0026 (14) |
C32 | 0.0422 (15) | 0.0573 (18) | 0.0510 (16) | −0.0027 (14) | 0.0255 (14) | 0.0013 (14) |
O1 | 0.0816 (17) | 0.0666 (16) | 0.0918 (18) | −0.0112 (13) | 0.0644 (15) | −0.0050 (14) |
O2 | 0.0906 (18) | 0.0586 (15) | 0.0659 (15) | 0.0090 (13) | 0.0444 (14) | 0.0070 (12) |
O3 | 0.115 (2) | 0.0606 (16) | 0.125 (3) | 0.0143 (16) | 0.090 (2) | 0.0101 (17) |
O4 | 0.1081 (18) | 0.0715 (15) | 0.0585 (12) | 0.0151 (13) | 0.0364 (13) | 0.0111 (11) |
O5 | 0.0614 (14) | 0.0711 (16) | 0.0638 (14) | 0.0187 (12) | 0.0329 (12) | 0.0094 (12) |
O6 | 0.096 (2) | 0.0750 (18) | 0.146 (3) | −0.0360 (16) | 0.092 (2) | −0.0488 (19) |
N1 | 0.0579 (15) | 0.0545 (15) | 0.0524 (15) | −0.0013 (12) | 0.0314 (13) | −0.0031 (12) |
N2 | 0.0697 (18) | 0.0615 (17) | 0.088 (2) | −0.0128 (14) | 0.0592 (17) | −0.0233 (14) |
N3 | 0.0554 (15) | 0.0481 (14) | 0.0540 (14) | −0.0052 (11) | 0.0339 (13) | −0.0116 (11) |
S1—O2 | 1.404 (3) | C15—H15A | 0.9300 |
S1—O1 | 1.432 (3) | C16—C17 | 1.375 (7) |
S1—N3 | 1.623 (3) | C16—C20 | 1.516 (6) |
S1—C1 | 1.786 (3) | C17—C18 | 1.385 (6) |
S2—O3 | 1.400 (3) | C17—H17A | 0.9300 |
S2—O6 | 1.424 (3) | C18—C19 | 1.510 (5) |
S2—N2 | 1.640 (3) | C19—H19A | 0.9600 |
S2—C13 | 1.773 (3) | C19—H19B | 0.9600 |
C1—C2 | 1.403 (5) | C19—H19C | 0.9600 |
C1—C6 | 1.408 (4) | C20—H20A | 0.9600 |
C2—C3 | 1.390 (5) | C20—H20B | 0.9600 |
C2—C9 | 1.526 (5) | C20—H20C | 0.9600 |
C3—C4 | 1.374 (6) | C21—H21A | 0.9600 |
C3—H3A | 0.9300 | C21—H21B | 0.9600 |
C4—C5 | 1.377 (6) | C21—H21C | 0.9600 |
C4—C8 | 1.515 (5) | C22—N2 | 1.473 (5) |
C5—C6 | 1.379 (5) | C22—C23 | 1.474 (5) |
C5—H5A | 0.9300 | C22—H22A | 0.9700 |
C6—C7 | 1.503 (5) | C22—H22B | 0.9700 |
C7—H7A | 0.9600 | C23—C24 | 1.513 (5) |
C7—H7B | 0.9600 | C23—H23A | 0.9700 |
C7—H7C | 0.9600 | C23—H23B | 0.9700 |
C8—H8A | 0.9600 | C24—N1 | 1.453 (4) |
C8—H8B | 0.9600 | C24—H24A | 0.9700 |
C8—H8C | 0.9600 | C24—H24B | 0.9700 |
C9—H9A | 0.9600 | C25—O4 | 1.199 (4) |
C9—H9B | 0.9600 | C25—N1 | 1.402 (5) |
C9—H9C | 0.9600 | C25—C26 | 1.479 (6) |
C10—N3 | 1.465 (4) | C26—C27 | 1.367 (5) |
C10—C11 | 1.520 (5) | C26—C31 | 1.386 (5) |
C10—H10A | 0.9700 | C27—C28 | 1.375 (6) |
C10—H10B | 0.9700 | C27—H27A | 0.9300 |
C11—C12 | 1.491 (6) | C28—C29 | 1.371 (6) |
C11—H11A | 0.9700 | C28—H28A | 0.9300 |
C11—H11B | 0.9700 | C29—C30 | 1.385 (5) |
C12—N2 | 1.516 (4) | C29—H29A | 0.9300 |
C12—H12A | 0.9700 | C30—C31 | 1.371 (5) |
C12—H12B | 0.9700 | C30—H30A | 0.9300 |
C13—C18 | 1.402 (5) | C31—C32 | 1.482 (5) |
C13—C14 | 1.410 (5) | C32—O5 | 1.205 (4) |
C14—C15 | 1.393 (5) | C32—N1 | 1.390 (4) |
C14—C21 | 1.498 (5) | N3—H3B | 0.8600 |
C15—C16 | 1.359 (7) | ||
O2—S1—O1 | 117.42 (17) | C17—C16—C20 | 120.9 (5) |
O2—S1—N3 | 107.70 (16) | C16—C17—C18 | 123.0 (4) |
O1—S1—N3 | 105.58 (15) | C16—C17—H17A | 118.5 |
O2—S1—C1 | 109.56 (15) | C18—C17—H17A | 118.5 |
O1—S1—C1 | 109.49 (15) | C17—C18—C13 | 117.6 (4) |
N3—S1—C1 | 106.49 (14) | C17—C18—C19 | 116.8 (4) |
O3—S2—O6 | 116.9 (2) | C13—C18—C19 | 125.6 (4) |
O3—S2—N2 | 110.94 (18) | C18—C19—H19A | 109.5 |
O6—S2—N2 | 106.63 (18) | C18—C19—H19B | 109.5 |
O3—S2—C13 | 108.23 (17) | H19A—C19—H19B | 109.5 |
O6—S2—C13 | 110.82 (17) | C18—C19—H19C | 109.5 |
N2—S2—C13 | 102.29 (16) | H19A—C19—H19C | 109.5 |
C2—C1—C6 | 120.5 (3) | H19B—C19—H19C | 109.5 |
C2—C1—S1 | 121.5 (2) | C16—C20—H20A | 109.5 |
C6—C1—S1 | 118.0 (2) | C16—C20—H20B | 109.5 |
C3—C2—C1 | 117.9 (3) | H20A—C20—H20B | 109.5 |
C3—C2—C9 | 116.3 (3) | C16—C20—H20C | 109.5 |
C1—C2—C9 | 125.8 (3) | H20A—C20—H20C | 109.5 |
C4—C3—C2 | 122.8 (4) | H20B—C20—H20C | 109.5 |
C4—C3—H3A | 118.6 | C14—C21—H21A | 109.5 |
C2—C3—H3A | 118.6 | C14—C21—H21B | 109.5 |
C3—C4—C5 | 117.7 (3) | H21A—C21—H21B | 109.5 |
C3—C4—C8 | 121.3 (4) | C14—C21—H21C | 109.5 |
C5—C4—C8 | 121.0 (4) | H21A—C21—H21C | 109.5 |
C4—C5—C6 | 123.0 (3) | H21B—C21—H21C | 109.5 |
C4—C5—H5A | 118.5 | N2—C22—C23 | 113.6 (3) |
C6—C5—H5A | 118.5 | N2—C22—H22A | 108.9 |
C5—C6—C1 | 118.1 (3) | C23—C22—H22A | 108.9 |
C5—C6—C7 | 116.9 (3) | N2—C22—H22B | 108.9 |
C1—C6—C7 | 125.1 (3) | C23—C22—H22B | 108.9 |
C6—C7—H7A | 109.5 | H22A—C22—H22B | 107.7 |
C6—C7—H7B | 109.5 | C22—C23—C24 | 113.9 (3) |
H7A—C7—H7B | 109.5 | C22—C23—H23A | 108.8 |
C6—C7—H7C | 109.5 | C24—C23—H23A | 108.8 |
H7A—C7—H7C | 109.5 | C22—C23—H23B | 108.8 |
H7B—C7—H7C | 109.5 | C24—C23—H23B | 108.8 |
C4—C8—H8A | 109.5 | H23A—C23—H23B | 107.7 |
C4—C8—H8B | 109.5 | N1—C24—C23 | 112.4 (3) |
H8A—C8—H8B | 109.5 | N1—C24—H24A | 109.1 |
C4—C8—H8C | 109.5 | C23—C24—H24A | 109.1 |
H8A—C8—H8C | 109.5 | N1—C24—H24B | 109.1 |
H8B—C8—H8C | 109.5 | C23—C24—H24B | 109.1 |
C2—C9—H9A | 109.5 | H24A—C24—H24B | 107.9 |
C2—C9—H9B | 109.5 | O4—C25—N1 | 123.8 (4) |
H9A—C9—H9B | 109.5 | O4—C25—C26 | 130.2 (4) |
C2—C9—H9C | 109.5 | N1—C25—C26 | 105.9 (3) |
H9A—C9—H9C | 109.5 | C27—C26—C31 | 121.3 (4) |
H9B—C9—H9C | 109.5 | C27—C26—C25 | 130.6 (3) |
N3—C10—C11 | 109.5 (3) | C31—C26—C25 | 108.0 (3) |
N3—C10—H10A | 109.8 | C26—C27—C28 | 117.7 (4) |
C11—C10—H10A | 109.8 | C26—C27—H27A | 121.2 |
N3—C10—H10B | 109.8 | C28—C27—H27A | 121.2 |
C11—C10—H10B | 109.8 | C29—C28—C27 | 121.6 (4) |
H10A—C10—H10B | 108.2 | C29—C28—H28A | 119.2 |
C12—C11—C10 | 109.3 (3) | C27—C28—H28A | 119.2 |
C12—C11—H11A | 109.8 | C28—C29—C30 | 120.6 (4) |
C10—C11—H11A | 109.8 | C28—C29—H29A | 119.7 |
C12—C11—H11B | 109.8 | C30—C29—H29A | 119.7 |
C10—C11—H11B | 109.8 | C31—C30—C29 | 118.0 (3) |
H11A—C11—H11B | 108.3 | C31—C30—H30A | 121.0 |
C11—C12—N2 | 113.7 (3) | C29—C30—H30A | 121.0 |
C11—C12—H12A | 108.8 | C30—C31—C26 | 120.8 (3) |
N2—C12—H12A | 108.8 | C30—C31—C32 | 130.9 (3) |
C11—C12—H12B | 108.8 | C26—C31—C32 | 108.4 (3) |
N2—C12—H12B | 108.8 | O5—C32—N1 | 124.9 (3) |
H12A—C12—H12B | 107.7 | O5—C32—C31 | 129.1 (3) |
C18—C13—C14 | 121.0 (3) | N1—C32—C31 | 105.9 (3) |
C18—C13—S2 | 116.5 (3) | C32—N1—C25 | 111.7 (3) |
C14—C13—S2 | 122.4 (3) | C32—N1—C24 | 125.1 (3) |
C15—C14—C13 | 117.0 (3) | C25—N1—C24 | 123.2 (3) |
C15—C14—C21 | 116.9 (3) | C22—N2—C12 | 119.1 (3) |
C13—C14—C21 | 126.0 (3) | C22—N2—S2 | 114.7 (2) |
C16—C15—C14 | 123.4 (4) | C12—N2—S2 | 118.8 (2) |
C16—C15—H15A | 118.3 | C10—N3—S1 | 118.2 (2) |
C14—C15—H15A | 118.3 | C10—N3—H3B | 120.9 |
C15—C16—C17 | 117.9 (4) | S1—N3—H3B | 120.9 |
C15—C16—C20 | 121.2 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3B···O5i | 0.86 | 2.53 | 3.192 (4) | 134 |
Symmetry code: (i) −x+1/2, y−1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C32H39N3O6S2 |
Mr | 625.78 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 296 |
a, b, c (Å) | 32.042 (3), 9.9782 (8), 25.105 (2) |
β (°) | 127.917 (1) |
V (Å3) | 6332.1 (9) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.18 × 0.15 × 0.13 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2001) |
Tmin, Tmax | 0.962, 0.973 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17128, 6212, 4574 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.069, 0.219, 1.10 |
No. of reflections | 6212 |
No. of parameters | 388 |
No. of restraints | 44 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.80, −0.57 |
Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3B···O5i | 0.86 | 2.53 | 3.192 (4) | 134 |
Symmetry code: (i) −x+1/2, y−1/2, −z+3/2. |
Polyamines are essential growth factors for cells, which exist mainly as polycations at physiological pH (Cullis et al., 1999; Seiler et al., 1996; Tsen et al., 2008). As part of our studies in this area, herein we report the synthesis and structure of the title compound, (I).
The compound (I) consists of a polyamine chain with two 2,4,6-trimethylbenzenesulfonyl group acting as protecting groups (Fig. 1). In the structure of (I), the two phenyl ring of two 2,4,6-trimethylbenzenesulfonyl group are nonparallel due to steric hindrance, charactrtized by a dihedral angel of 27.1 (3) °.
In the crystal, molecules are linked through intermolecular N–H···O hydrogen bonds to construct an infinite one-dimensional chain (Fig. 2 and Table 1).