The title compound, C
42H
44N
2O
8S
2, features a molecular thread. The molecules have crystallographic
Ci symmetry. The crystal packing shows staples stabilized by weak C—H
O interactions.
Supporting information
CCDC reference: 298374
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean (C-C) = 0.002 Å
- R factor = 0.033
- wR factor = 0.093
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.93
| Author Response: Data were collected using an early bete-test version of the
COLLECT-software. Only \f-scans without \q-offset were possible. The
completeness for 2\q = 50\% is only 93%.
|
Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
From the CIF: _diffrn_reflns_theta_max 28.26
From the CIF: _reflns_number_total 3582
From the CIF: _diffrn_reflns_limit_ max hkl 8. 14. 15.
From the CIF: _diffrn_reflns_limit_ min hkl -8. -14. -15.
TEST1: Expected hkl limits for theta max
Calculated maximum hkl 8. 15. 17.
Calculated minimum hkl -8. -15. -17.
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
0 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
0 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
Data collection: COLLECT (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXL97.
1,4-Bis{
N-[4-(ethoxycarbonyl)benzyl]-
N-(4-tolylsulfonyl)aminomethyl}benzene
top
Crystal data top
C42H44N2O8S2 | Z = 1 |
Mr = 768.91 | F(000) = 406 |
Triclinic, P1 | Dx = 1.320 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.7007 (2) Å | Cell parameters from 15013 reflections |
b = 11.7108 (5) Å | θ = 3.2–28.3° |
c = 13.1888 (5) Å | µ = 0.19 mm−1 |
α = 78.912 (2)° | T = 123 K |
β = 80.801 (2)° | Plates, colourless |
γ = 73.492 (2)° | 0.35 × 0.30 × 0.05 mm |
V = 967.64 (6) Å3 | |
Data collection top
Nonius KappaCCD diffractometer | 3145 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.021 |
Graphite monochromator | θmax = 28.3°, θmin = 3.2° |
rotation in φ, 2° scans | h = −8→8 |
15012 measured reflections | k = −14→14 |
3582 independent reflections | l = −15→15 |
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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0481P)2 + 0.2922P] where P = (Fo2 + 2Fc2)/3 |
3582 reflections | (Δ/σ)max = 0.001 |
245 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
Special details top
Experimental. dx = 29 mm; mos.= 0.671 (2)°., 150 sec/°, 200 frames, 2°. Data were collected
using an early bete-test version of the COLLECT-software. Only φ-scans
without θ-offset were possible. The completeness for 2θ = 50° is only 93%. |
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 | |
C1 | 0.4984 (2) | 0.65949 (12) | 0.30046 (10) | 0.0283 (3) | |
H1A | 0.3758 | 0.7304 | 0.3030 | 0.034* | |
H1B | 0.6263 | 0.6889 | 0.2868 | 0.034* | |
N2 | 0.49049 (18) | 0.59688 (10) | 0.21448 (9) | 0.0273 (3) | |
C3 | 0.6894 (2) | 0.53321 (13) | 0.16246 (11) | 0.0322 (3) | |
H3A | 0.7953 | 0.5777 | 0.1613 | 0.039* | |
H3B | 0.6707 | 0.5333 | 0.0895 | 0.039* | |
C11 | 0.4990 (2) | 0.57808 (11) | 0.40480 (10) | 0.0251 (3) | |
C12 | 0.6828 (2) | 0.52703 (12) | 0.45081 (10) | 0.0274 (3) | |
H12 | 0.8091 | 0.5453 | 0.4174 | 0.033* | |
C13 | 0.6850 (2) | 0.44970 (12) | 0.54493 (10) | 0.0275 (3) | |
H13 | 0.8124 | 0.4155 | 0.5753 | 0.033* | |
S2 | 0.28165 (5) | 0.63536 (3) | 0.15451 (3) | 0.02748 (11) | |
O21 | 0.29672 (18) | 0.54015 (9) | 0.09724 (8) | 0.0374 (3) | |
O22 | 0.10614 (16) | 0.66712 (9) | 0.23119 (8) | 0.0331 (2) | |
C23 | 0.2911 (2) | 0.76617 (13) | 0.06414 (10) | 0.0287 (3) | |
C24 | 0.3742 (2) | 0.75645 (15) | −0.03863 (11) | 0.0349 (3) | |
H24 | 0.4235 | 0.6799 | −0.0610 | 0.042* | |
C25 | 0.3832 (2) | 0.86099 (16) | −0.10753 (12) | 0.0407 (4) | |
H25 | 0.4386 | 0.8552 | −0.1779 | 0.049* | |
C26 | 0.3136 (2) | 0.97381 (15) | −0.07668 (13) | 0.0404 (4) | |
C27 | 0.2345 (3) | 0.98064 (14) | 0.02642 (13) | 0.0387 (4) | |
H27 | 0.1878 | 1.0571 | 0.0490 | 0.046* | |
C28 | 0.2223 (2) | 0.87802 (13) | 0.09710 (11) | 0.0321 (3) | |
H28 | 0.1674 | 0.8841 | 0.1674 | 0.039* | |
C29 | 0.3215 (3) | 1.08596 (18) | −0.15428 (16) | 0.0579 (6) | |
H29A | 0.4504 | 1.0697 | −0.2023 | 0.087* | |
H29B | 0.3195 | 1.1514 | −0.1174 | 0.087* | |
H29C | 0.1999 | 1.1096 | −0.1935 | 0.087* | |
C31 | 0.7718 (2) | 0.40369 (12) | 0.21379 (11) | 0.0289 (3) | |
C32 | 0.6429 (2) | 0.34215 (12) | 0.28211 (11) | 0.0316 (3) | |
H32 | 0.5003 | 0.3820 | 0.2997 | 0.038* | |
C33 | 0.7220 (2) | 0.22236 (13) | 0.32479 (12) | 0.0335 (3) | |
H33 | 0.6338 | 0.1813 | 0.3725 | 0.040* | |
C34 | 0.9281 (2) | 0.16269 (13) | 0.29817 (11) | 0.0332 (3) | |
C35 | 1.0573 (3) | 0.22446 (14) | 0.23012 (13) | 0.0397 (4) | |
H35 | 1.1995 | 0.1843 | 0.2119 | 0.048* | |
C36 | 0.9792 (2) | 0.34431 (14) | 0.18887 (12) | 0.0371 (4) | |
H36 | 1.0689 | 0.3861 | 0.1431 | 0.045* | |
C37 | 1.0153 (3) | 0.03273 (13) | 0.33856 (12) | 0.0367 (4) | |
O37 | 1.19523 (19) | −0.02306 (10) | 0.32096 (9) | 0.0474 (3) | |
O38 | 0.86780 (19) | −0.01640 (9) | 0.39566 (9) | 0.0437 (3) | |
C38 | 0.9336 (3) | −0.14474 (13) | 0.43493 (14) | 0.0459 (4) | |
H38A | 1.0511 | −0.1622 | 0.4773 | 0.055* | |
H38B | 0.9796 | −0.1918 | 0.3767 | 0.055* | |
C39 | 0.7456 (3) | −0.17623 (16) | 0.50028 (15) | 0.0545 (5) | |
H39A | 0.7815 | −0.2624 | 0.5286 | 0.082* | |
H39B | 0.6306 | −0.1579 | 0.4573 | 0.082* | |
H39C | 0.7023 | −0.1290 | 0.5576 | 0.082* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0351 (9) | 0.0215 (6) | 0.0294 (7) | −0.0099 (6) | −0.0084 (5) | 0.0012 (5) |
N2 | 0.0290 (7) | 0.0238 (5) | 0.0272 (6) | −0.0047 (5) | −0.0058 (4) | −0.0008 (4) |
C3 | 0.0293 (9) | 0.0295 (7) | 0.0337 (8) | −0.0068 (6) | 0.0009 (6) | −0.0003 (6) |
C11 | 0.0314 (8) | 0.0178 (6) | 0.0266 (7) | −0.0076 (5) | −0.0064 (5) | −0.0005 (5) |
C12 | 0.0272 (8) | 0.0251 (6) | 0.0306 (7) | −0.0098 (6) | −0.0045 (5) | −0.0005 (5) |
C13 | 0.0265 (8) | 0.0245 (6) | 0.0309 (7) | −0.0055 (6) | −0.0093 (5) | 0.0001 (5) |
S2 | 0.0303 (2) | 0.02588 (18) | 0.02771 (19) | −0.01124 (14) | −0.00551 (13) | 0.00010 (13) |
O21 | 0.0477 (7) | 0.0330 (6) | 0.0384 (6) | −0.0201 (5) | −0.0055 (5) | −0.0073 (4) |
O22 | 0.0298 (6) | 0.0338 (5) | 0.0333 (5) | −0.0099 (4) | −0.0025 (4) | 0.0019 (4) |
C23 | 0.0285 (8) | 0.0317 (7) | 0.0282 (7) | −0.0125 (6) | −0.0101 (5) | 0.0024 (5) |
C24 | 0.0319 (9) | 0.0437 (9) | 0.0317 (8) | −0.0155 (7) | −0.0081 (6) | −0.0001 (6) |
C25 | 0.0309 (9) | 0.0606 (11) | 0.0306 (8) | −0.0199 (8) | −0.0094 (6) | 0.0097 (7) |
C26 | 0.0254 (9) | 0.0476 (9) | 0.0467 (9) | −0.0168 (7) | −0.0174 (6) | 0.0187 (7) |
C27 | 0.0338 (9) | 0.0321 (8) | 0.0511 (10) | −0.0114 (7) | −0.0193 (7) | 0.0080 (7) |
C28 | 0.0320 (9) | 0.0315 (7) | 0.0334 (8) | −0.0093 (6) | −0.0125 (6) | 0.0022 (6) |
C29 | 0.0365 (11) | 0.0599 (11) | 0.0682 (12) | −0.0206 (9) | −0.0212 (8) | 0.0368 (10) |
C31 | 0.0292 (8) | 0.0270 (7) | 0.0301 (7) | −0.0076 (6) | −0.0016 (5) | −0.0044 (5) |
C32 | 0.0268 (8) | 0.0258 (7) | 0.0386 (8) | −0.0049 (6) | 0.0039 (6) | −0.0057 (6) |
C33 | 0.0328 (9) | 0.0258 (7) | 0.0384 (8) | −0.0075 (6) | 0.0056 (6) | −0.0043 (6) |
C34 | 0.0339 (9) | 0.0264 (7) | 0.0352 (8) | −0.0035 (6) | 0.0009 (6) | −0.0059 (6) |
C35 | 0.0271 (9) | 0.0368 (8) | 0.0471 (9) | −0.0019 (7) | 0.0044 (6) | −0.0040 (7) |
C36 | 0.0290 (9) | 0.0367 (8) | 0.0414 (9) | −0.0098 (7) | 0.0035 (6) | 0.0001 (6) |
C37 | 0.0386 (10) | 0.0292 (7) | 0.0366 (8) | −0.0013 (7) | 0.0015 (6) | −0.0077 (6) |
O37 | 0.0418 (8) | 0.0345 (6) | 0.0516 (7) | 0.0057 (5) | 0.0046 (5) | −0.0040 (5) |
O38 | 0.0454 (7) | 0.0227 (5) | 0.0542 (7) | −0.0035 (5) | 0.0073 (5) | −0.0038 (5) |
C38 | 0.0621 (12) | 0.0216 (7) | 0.0459 (9) | −0.0033 (7) | 0.0027 (8) | −0.0048 (6) |
C39 | 0.0738 (14) | 0.0327 (9) | 0.0566 (11) | −0.0205 (9) | 0.0062 (9) | −0.0070 (8) |
Geometric parameters (Å, º) top
C1—N2 | 1.4790 (17) | C27—C28 | 1.386 (2) |
C1—C11 | 1.5159 (18) | C27—H27 | 0.9500 |
C1—H1A | 0.9900 | C28—H28 | 0.9500 |
C1—H1B | 0.9900 | C29—H29A | 0.9800 |
N2—C3 | 1.4637 (18) | C29—H29B | 0.9800 |
N2—S2 | 1.6265 (12) | C29—H29C | 0.9800 |
C3—C31 | 1.5207 (19) | C31—C36 | 1.384 (2) |
C3—H3A | 0.9900 | C31—C32 | 1.3902 (19) |
C3—H3B | 0.9900 | C32—C33 | 1.391 (2) |
C11—C12 | 1.3872 (19) | C32—H32 | 0.9500 |
C11—C13i | 1.3960 (19) | C33—C34 | 1.382 (2) |
C12—C13 | 1.3882 (19) | C33—H33 | 0.9500 |
C12—H12 | 0.9500 | C34—C35 | 1.391 (2) |
C13—C11i | 1.3960 (19) | C34—C37 | 1.491 (2) |
C13—H13 | 0.9500 | C35—C36 | 1.386 (2) |
S2—O21 | 1.4351 (10) | C35—H35 | 0.9500 |
S2—O22 | 1.4353 (10) | C36—H36 | 0.9500 |
S2—C23 | 1.7608 (14) | C37—O37 | 1.2066 (19) |
C23—C28 | 1.389 (2) | C37—O38 | 1.3392 (19) |
C23—C24 | 1.394 (2) | O38—C38 | 1.4555 (18) |
C24—C25 | 1.387 (2) | C38—C39 | 1.503 (3) |
C24—H24 | 0.9500 | C38—H38A | 0.9900 |
C25—C26 | 1.387 (3) | C38—H38B | 0.9900 |
C25—H25 | 0.9500 | C39—H39A | 0.9800 |
C26—C27 | 1.387 (2) | C39—H39B | 0.9800 |
C26—C29 | 1.510 (2) | C39—H39C | 0.9800 |
| | | |
N2—C1—C11 | 112.18 (10) | C26—C27—H27 | 119.4 |
N2—C1—H1A | 109.2 | C27—C28—C23 | 119.37 (14) |
C11—C1—H1A | 109.2 | C27—C28—H28 | 120.3 |
N2—C1—H1B | 109.2 | C23—C28—H28 | 120.3 |
C11—C1—H1B | 109.2 | C26—C29—H29A | 109.5 |
H1A—C1—H1B | 107.9 | C26—C29—H29B | 109.5 |
C3—N2—C1 | 117.85 (11) | H29A—C29—H29B | 109.5 |
C3—N2—S2 | 118.94 (9) | C26—C29—H29C | 109.5 |
C1—N2—S2 | 119.90 (9) | H29A—C29—H29C | 109.5 |
N2—C3—C31 | 113.79 (11) | H29B—C29—H29C | 109.5 |
N2—C3—H3A | 108.8 | C36—C31—C32 | 119.21 (14) |
C31—C3—H3A | 108.8 | C36—C31—C3 | 118.94 (13) |
N2—C3—H3B | 108.8 | C32—C31—C3 | 121.81 (13) |
C31—C3—H3B | 108.8 | C31—C32—C33 | 120.22 (14) |
H3A—C3—H3B | 107.7 | C31—C32—H32 | 119.9 |
C12—C11—C13i | 118.69 (12) | C33—C32—H32 | 119.9 |
C12—C11—C1 | 120.81 (12) | C34—C33—C32 | 120.40 (14) |
C13i—C11—C1 | 120.47 (12) | C34—C33—H33 | 119.8 |
C11—C12—C13 | 120.96 (13) | C32—C33—H33 | 119.8 |
C11—C12—H12 | 119.5 | C33—C34—C35 | 119.34 (14) |
C13—C12—H12 | 119.5 | C33—C34—C37 | 121.79 (14) |
C12—C13—C11i | 120.35 (13) | C35—C34—C37 | 118.85 (14) |
C12—C13—H13 | 119.8 | C36—C35—C34 | 120.22 (15) |
C11i—C13—H13 | 119.8 | C36—C35—H35 | 119.9 |
O21—S2—O22 | 119.90 (6) | C34—C35—H35 | 119.9 |
O21—S2—N2 | 106.69 (6) | C31—C36—C35 | 120.59 (14) |
O22—S2—N2 | 106.64 (6) | C31—C36—H36 | 119.7 |
O21—S2—C23 | 107.78 (6) | C35—C36—H36 | 119.7 |
O22—S2—C23 | 107.71 (6) | O37—C37—O38 | 123.47 (14) |
N2—S2—C23 | 107.58 (6) | O37—C37—C34 | 124.81 (15) |
C28—C23—C24 | 120.60 (13) | O38—C37—C34 | 111.71 (13) |
C28—C23—S2 | 119.45 (11) | C37—O38—C38 | 116.35 (13) |
C24—C23—S2 | 119.91 (11) | O38—C38—C39 | 106.11 (14) |
C25—C24—C23 | 118.56 (15) | O38—C38—H38A | 110.5 |
C25—C24—H24 | 120.7 | C39—C38—H38A | 110.5 |
C23—C24—H24 | 120.7 | O38—C38—H38B | 110.5 |
C26—C25—C24 | 121.89 (15) | C39—C38—H38B | 110.5 |
C26—C25—H25 | 119.1 | H38A—C38—H38B | 108.7 |
C24—C25—H25 | 119.1 | C38—C39—H39A | 109.5 |
C27—C26—C25 | 118.31 (14) | C38—C39—H39B | 109.5 |
C27—C26—C29 | 121.21 (17) | H39A—C39—H39B | 109.5 |
C25—C26—C29 | 120.47 (17) | C38—C39—H39C | 109.5 |
C28—C27—C26 | 121.26 (16) | H39A—C39—H39C | 109.5 |
C28—C27—H27 | 119.4 | H39B—C39—H39C | 109.5 |
| | | |
C11—C1—N2—C3 | −89.30 (14) | C24—C25—C26—C29 | −178.71 (14) |
C11—C1—N2—S2 | 111.45 (12) | C25—C26—C27—C28 | −0.8 (2) |
C1—N2—C3—C31 | 87.75 (15) | C29—C26—C27—C28 | 178.37 (14) |
S2—N2—C3—C31 | −112.79 (12) | C26—C27—C28—C23 | 0.2 (2) |
N2—C1—C11—C12 | 102.38 (14) | C24—C23—C28—C27 | 0.8 (2) |
N2—C1—C11—C13i | −75.78 (16) | S2—C23—C28—C27 | 178.48 (11) |
C13i—C11—C12—C13 | 0.1 (2) | N2—C3—C31—C36 | −163.97 (13) |
C1—C11—C12—C13 | −178.14 (12) | N2—C3—C31—C32 | 18.3 (2) |
C11—C12—C13—C11i | −0.1 (2) | C36—C31—C32—C33 | 0.0 (2) |
C3—N2—S2—O21 | 36.46 (11) | C3—C31—C32—C33 | 177.74 (13) |
C1—N2—S2—O21 | −164.51 (10) | C31—C32—C33—C34 | −1.3 (2) |
C3—N2—S2—O22 | 165.72 (10) | C32—C33—C34—C35 | 1.5 (2) |
C1—N2—S2—O22 | −35.26 (11) | C32—C33—C34—C37 | −177.08 (14) |
C3—N2—S2—C23 | −78.96 (11) | C33—C34—C35—C36 | −0.5 (2) |
C1—N2—S2—C23 | 80.07 (11) | C37—C34—C35—C36 | 178.11 (15) |
O21—S2—C23—C28 | 162.16 (11) | C32—C31—C36—C35 | 1.0 (2) |
O22—S2—C23—C28 | 31.48 (13) | C3—C31—C36—C35 | −176.82 (14) |
N2—S2—C23—C28 | −83.14 (13) | C34—C35—C36—C31 | −0.7 (3) |
O21—S2—C23—C24 | −20.11 (14) | C33—C34—C37—O37 | −177.37 (16) |
O22—S2—C23—C24 | −150.79 (11) | C35—C34—C37—O37 | 4.0 (3) |
N2—S2—C23—C24 | 94.60 (12) | C33—C34—C37—O38 | 4.0 (2) |
C28—C23—C24—C25 | −1.1 (2) | C35—C34—C37—O38 | −174.64 (14) |
S2—C23—C24—C25 | −178.79 (11) | O37—C37—O38—C38 | −1.5 (2) |
C23—C24—C25—C26 | 0.5 (2) | C34—C37—O38—C38 | 177.15 (13) |
C24—C25—C26—C27 | 0.4 (2) | C37—O38—C38—C39 | 177.09 (15) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C28—H28···O37ii | 0.95 | 2.53 | 3.3341 (19) | 143 |
Symmetry code: (ii) x−1, y+1, z. |