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The title compound, C42H44N2O8S2, features a mol­ecular thread. The mol­ecules have crystallographic Ci symmetry. The crystal packing shows staples stabilized by weak C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806000742/bt6800sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806000742/bt6800Isup2.hkl
Contains datablock I

CCDC reference: 298374

Key indicators

  • Single-crystal X-ray study
  • T = 123 K
  • Mean [sigma](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

Computing details top

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
C42H44N2O8S2Z = 1
Mr = 768.91F(000) = 406
Triclinic, P1Dx = 1.320 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.7007 (2) ÅCell parameters from 15013 reflections
b = 11.7108 (5) Åθ = 3.2–28.3°
c = 13.1888 (5) ŵ = 0.19 mm1
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 tubeRint = 0.021
Graphite monochromatorθmax = 28.3°, θmin = 3.2°
rotation in φ, 2° scansh = 88
15012 measured reflectionsk = 1414
3582 independent reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H-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 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.38 e Å3
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
xyzUiso*/Ueq
C10.4984 (2)0.65949 (12)0.30046 (10)0.0283 (3)
H1A0.37580.73040.30300.034*
H1B0.62630.68890.28680.034*
N20.49049 (18)0.59688 (10)0.21448 (9)0.0273 (3)
C30.6894 (2)0.53321 (13)0.16246 (11)0.0322 (3)
H3A0.79530.57770.16130.039*
H3B0.67070.53330.08950.039*
C110.4990 (2)0.57808 (11)0.40480 (10)0.0251 (3)
C120.6828 (2)0.52703 (12)0.45081 (10)0.0274 (3)
H120.80910.54530.41740.033*
C130.6850 (2)0.44970 (12)0.54493 (10)0.0275 (3)
H130.81240.41550.57530.033*
S20.28165 (5)0.63536 (3)0.15451 (3)0.02748 (11)
O210.29672 (18)0.54015 (9)0.09724 (8)0.0374 (3)
O220.10614 (16)0.66712 (9)0.23119 (8)0.0331 (2)
C230.2911 (2)0.76617 (13)0.06414 (10)0.0287 (3)
C240.3742 (2)0.75645 (15)0.03863 (11)0.0349 (3)
H240.42350.67990.06100.042*
C250.3832 (2)0.86099 (16)0.10753 (12)0.0407 (4)
H250.43860.85520.17790.049*
C260.3136 (2)0.97381 (15)0.07668 (13)0.0404 (4)
C270.2345 (3)0.98064 (14)0.02642 (13)0.0387 (4)
H270.18781.05710.04900.046*
C280.2223 (2)0.87802 (13)0.09710 (11)0.0321 (3)
H280.16740.88410.16740.039*
C290.3215 (3)1.08596 (18)0.15428 (16)0.0579 (6)
H29A0.45041.06970.20230.087*
H29B0.31951.15140.11740.087*
H29C0.19991.10960.19350.087*
C310.7718 (2)0.40369 (12)0.21379 (11)0.0289 (3)
C320.6429 (2)0.34215 (12)0.28211 (11)0.0316 (3)
H320.50030.38200.29970.038*
C330.7220 (2)0.22236 (13)0.32479 (12)0.0335 (3)
H330.63380.18130.37250.040*
C340.9281 (2)0.16269 (13)0.29817 (11)0.0332 (3)
C351.0573 (3)0.22446 (14)0.23012 (13)0.0397 (4)
H351.19950.18430.21190.048*
C360.9792 (2)0.34431 (14)0.18887 (12)0.0371 (4)
H361.06890.38610.14310.045*
C371.0153 (3)0.03273 (13)0.33856 (12)0.0367 (4)
O371.19523 (19)0.02306 (10)0.32096 (9)0.0474 (3)
O380.86780 (19)0.01640 (9)0.39566 (9)0.0437 (3)
C380.9336 (3)0.14474 (13)0.43493 (14)0.0459 (4)
H38A1.05110.16220.47730.055*
H38B0.97960.19180.37670.055*
C390.7456 (3)0.17623 (16)0.50028 (15)0.0545 (5)
H39A0.78150.26240.52860.082*
H39B0.63060.15790.45730.082*
H39C0.70230.12900.55760.082*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0351 (9)0.0215 (6)0.0294 (7)0.0099 (6)0.0084 (5)0.0012 (5)
N20.0290 (7)0.0238 (5)0.0272 (6)0.0047 (5)0.0058 (4)0.0008 (4)
C30.0293 (9)0.0295 (7)0.0337 (8)0.0068 (6)0.0009 (6)0.0003 (6)
C110.0314 (8)0.0178 (6)0.0266 (7)0.0076 (5)0.0064 (5)0.0005 (5)
C120.0272 (8)0.0251 (6)0.0306 (7)0.0098 (6)0.0045 (5)0.0005 (5)
C130.0265 (8)0.0245 (6)0.0309 (7)0.0055 (6)0.0093 (5)0.0001 (5)
S20.0303 (2)0.02588 (18)0.02771 (19)0.01124 (14)0.00551 (13)0.00010 (13)
O210.0477 (7)0.0330 (6)0.0384 (6)0.0201 (5)0.0055 (5)0.0073 (4)
O220.0298 (6)0.0338 (5)0.0333 (5)0.0099 (4)0.0025 (4)0.0019 (4)
C230.0285 (8)0.0317 (7)0.0282 (7)0.0125 (6)0.0101 (5)0.0024 (5)
C240.0319 (9)0.0437 (9)0.0317 (8)0.0155 (7)0.0081 (6)0.0001 (6)
C250.0309 (9)0.0606 (11)0.0306 (8)0.0199 (8)0.0094 (6)0.0097 (7)
C260.0254 (9)0.0476 (9)0.0467 (9)0.0168 (7)0.0174 (6)0.0187 (7)
C270.0338 (9)0.0321 (8)0.0511 (10)0.0114 (7)0.0193 (7)0.0080 (7)
C280.0320 (9)0.0315 (7)0.0334 (8)0.0093 (6)0.0125 (6)0.0022 (6)
C290.0365 (11)0.0599 (11)0.0682 (12)0.0206 (9)0.0212 (8)0.0368 (10)
C310.0292 (8)0.0270 (7)0.0301 (7)0.0076 (6)0.0016 (5)0.0044 (5)
C320.0268 (8)0.0258 (7)0.0386 (8)0.0049 (6)0.0039 (6)0.0057 (6)
C330.0328 (9)0.0258 (7)0.0384 (8)0.0075 (6)0.0056 (6)0.0043 (6)
C340.0339 (9)0.0264 (7)0.0352 (8)0.0035 (6)0.0009 (6)0.0059 (6)
C350.0271 (9)0.0368 (8)0.0471 (9)0.0019 (7)0.0044 (6)0.0040 (7)
C360.0290 (9)0.0367 (8)0.0414 (9)0.0098 (7)0.0035 (6)0.0001 (6)
C370.0386 (10)0.0292 (7)0.0366 (8)0.0013 (7)0.0015 (6)0.0077 (6)
O370.0418 (8)0.0345 (6)0.0516 (7)0.0057 (5)0.0046 (5)0.0040 (5)
O380.0454 (7)0.0227 (5)0.0542 (7)0.0035 (5)0.0073 (5)0.0038 (5)
C380.0621 (12)0.0216 (7)0.0459 (9)0.0033 (7)0.0027 (8)0.0048 (6)
C390.0738 (14)0.0327 (9)0.0566 (11)0.0205 (9)0.0062 (9)0.0070 (8)
Geometric parameters (Å, º) top
C1—N21.4790 (17)C27—C281.386 (2)
C1—C111.5159 (18)C27—H270.9500
C1—H1A0.9900C28—H280.9500
C1—H1B0.9900C29—H29A0.9800
N2—C31.4637 (18)C29—H29B0.9800
N2—S21.6265 (12)C29—H29C0.9800
C3—C311.5207 (19)C31—C361.384 (2)
C3—H3A0.9900C31—C321.3902 (19)
C3—H3B0.9900C32—C331.391 (2)
C11—C121.3872 (19)C32—H320.9500
C11—C13i1.3960 (19)C33—C341.382 (2)
C12—C131.3882 (19)C33—H330.9500
C12—H120.9500C34—C351.391 (2)
C13—C11i1.3960 (19)C34—C371.491 (2)
C13—H130.9500C35—C361.386 (2)
S2—O211.4351 (10)C35—H350.9500
S2—O221.4353 (10)C36—H360.9500
S2—C231.7608 (14)C37—O371.2066 (19)
C23—C281.389 (2)C37—O381.3392 (19)
C23—C241.394 (2)O38—C381.4555 (18)
C24—C251.387 (2)C38—C391.503 (3)
C24—H240.9500C38—H38A0.9900
C25—C261.387 (3)C38—H38B0.9900
C25—H250.9500C39—H39A0.9800
C26—C271.387 (2)C39—H39B0.9800
C26—C291.510 (2)C39—H39C0.9800
N2—C1—C11112.18 (10)C26—C27—H27119.4
N2—C1—H1A109.2C27—C28—C23119.37 (14)
C11—C1—H1A109.2C27—C28—H28120.3
N2—C1—H1B109.2C23—C28—H28120.3
C11—C1—H1B109.2C26—C29—H29A109.5
H1A—C1—H1B107.9C26—C29—H29B109.5
C3—N2—C1117.85 (11)H29A—C29—H29B109.5
C3—N2—S2118.94 (9)C26—C29—H29C109.5
C1—N2—S2119.90 (9)H29A—C29—H29C109.5
N2—C3—C31113.79 (11)H29B—C29—H29C109.5
N2—C3—H3A108.8C36—C31—C32119.21 (14)
C31—C3—H3A108.8C36—C31—C3118.94 (13)
N2—C3—H3B108.8C32—C31—C3121.81 (13)
C31—C3—H3B108.8C31—C32—C33120.22 (14)
H3A—C3—H3B107.7C31—C32—H32119.9
C12—C11—C13i118.69 (12)C33—C32—H32119.9
C12—C11—C1120.81 (12)C34—C33—C32120.40 (14)
C13i—C11—C1120.47 (12)C34—C33—H33119.8
C11—C12—C13120.96 (13)C32—C33—H33119.8
C11—C12—H12119.5C33—C34—C35119.34 (14)
C13—C12—H12119.5C33—C34—C37121.79 (14)
C12—C13—C11i120.35 (13)C35—C34—C37118.85 (14)
C12—C13—H13119.8C36—C35—C34120.22 (15)
C11i—C13—H13119.8C36—C35—H35119.9
O21—S2—O22119.90 (6)C34—C35—H35119.9
O21—S2—N2106.69 (6)C31—C36—C35120.59 (14)
O22—S2—N2106.64 (6)C31—C36—H36119.7
O21—S2—C23107.78 (6)C35—C36—H36119.7
O22—S2—C23107.71 (6)O37—C37—O38123.47 (14)
N2—S2—C23107.58 (6)O37—C37—C34124.81 (15)
C28—C23—C24120.60 (13)O38—C37—C34111.71 (13)
C28—C23—S2119.45 (11)C37—O38—C38116.35 (13)
C24—C23—S2119.91 (11)O38—C38—C39106.11 (14)
C25—C24—C23118.56 (15)O38—C38—H38A110.5
C25—C24—H24120.7C39—C38—H38A110.5
C23—C24—H24120.7O38—C38—H38B110.5
C26—C25—C24121.89 (15)C39—C38—H38B110.5
C26—C25—H25119.1H38A—C38—H38B108.7
C24—C25—H25119.1C38—C39—H39A109.5
C27—C26—C25118.31 (14)C38—C39—H39B109.5
C27—C26—C29121.21 (17)H39A—C39—H39B109.5
C25—C26—C29120.47 (17)C38—C39—H39C109.5
C28—C27—C26121.26 (16)H39A—C39—H39C109.5
C28—C27—H27119.4H39B—C39—H39C109.5
C11—C1—N2—C389.30 (14)C24—C25—C26—C29178.71 (14)
C11—C1—N2—S2111.45 (12)C25—C26—C27—C280.8 (2)
C1—N2—C3—C3187.75 (15)C29—C26—C27—C28178.37 (14)
S2—N2—C3—C31112.79 (12)C26—C27—C28—C230.2 (2)
N2—C1—C11—C12102.38 (14)C24—C23—C28—C270.8 (2)
N2—C1—C11—C13i75.78 (16)S2—C23—C28—C27178.48 (11)
C13i—C11—C12—C130.1 (2)N2—C3—C31—C36163.97 (13)
C1—C11—C12—C13178.14 (12)N2—C3—C31—C3218.3 (2)
C11—C12—C13—C11i0.1 (2)C36—C31—C32—C330.0 (2)
C3—N2—S2—O2136.46 (11)C3—C31—C32—C33177.74 (13)
C1—N2—S2—O21164.51 (10)C31—C32—C33—C341.3 (2)
C3—N2—S2—O22165.72 (10)C32—C33—C34—C351.5 (2)
C1—N2—S2—O2235.26 (11)C32—C33—C34—C37177.08 (14)
C3—N2—S2—C2378.96 (11)C33—C34—C35—C360.5 (2)
C1—N2—S2—C2380.07 (11)C37—C34—C35—C36178.11 (15)
O21—S2—C23—C28162.16 (11)C32—C31—C36—C351.0 (2)
O22—S2—C23—C2831.48 (13)C3—C31—C36—C35176.82 (14)
N2—S2—C23—C2883.14 (13)C34—C35—C36—C310.7 (3)
O21—S2—C23—C2420.11 (14)C33—C34—C37—O37177.37 (16)
O22—S2—C23—C24150.79 (11)C35—C34—C37—O374.0 (3)
N2—S2—C23—C2494.60 (12)C33—C34—C37—O384.0 (2)
C28—C23—C24—C251.1 (2)C35—C34—C37—O38174.64 (14)
S2—C23—C24—C25178.79 (11)O37—C37—O38—C381.5 (2)
C23—C24—C25—C260.5 (2)C34—C37—O38—C38177.15 (13)
C24—C25—C26—C270.4 (2)C37—O38—C38—C39177.09 (15)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C28—H28···O37ii0.952.533.3341 (19)143
Symmetry code: (ii) x1, y+1, z.
 

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