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The title compound, C38H36N8O4S2, has a center of symmetry and the central six-membered ring shows a chair conformation. The dihedral angle between the ring carrying the tosyl group and the phthalo­nitrile ring is 36.98 (11)°. The crystal structure is stabilized by an intramolecular C—H...N and two intermolecular C—H...O close contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802012308/ob6149sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802012308/ob6149Isup2.hkl
Contains datablock I

CCDC reference: 193764

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.046
  • wR factor = 0.154
  • Data-to-parameter ratio = 17.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
GOODF_01 Alert C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.722 REFLT_03 From the CIF: _diffrn_reflns_theta_max 28.00 From the CIF: _reflns_number_total 4124 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 4528 Completeness (_total/calc) 91.08% Alert C: < 95% complete PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(1) - C(3) = 1.44 Ang. PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(2) - C(8) = 1.45 Ang.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
4 Alert Level C = Please check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); 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).

4,4'-[2,2'-(Piperidin-1,4-diyldiethylene)di(tosylimino)]diphthalonitrile top
Crystal data top
C38H36N8O4S2F(000) = 768
Mr = 732.89Dx = 1.295 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ycCell parameters from 9948 reflections
a = 8.4238 (11) Åθ = 1.4–28.0°
b = 29.217 (4) ŵ = 0.19 mm1
c = 7.7120 (11) ÅT = 293 K
β = 98.052 (3)°Prism, colourless
V = 1879.4 (5) Å30.21 × 0.19 × 0.06 mm
Z = 2
Data collection top
Bruker CCD area-detector
diffractometer
1241 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.078
Graphite monochromatorθmax = 28.0°, θmin = 1.4°
φ and ω scansh = 1011
9948 measured reflectionsk = 3338
4124 independent reflectionsl = 109
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154H-atom parameters constrained
S = 0.72 w = 1/[σ2(Fo2) + (0.0613P)2]
where P = (Fo2 + 2Fc2)/3
4124 reflections(Δ/σ)max < 0.001
235 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.19 e Å3
Special details top

Geometry. The ring formed by atoms C3—C8 is planar, with deviation from the plane for N1, N2, N3, C1 and C8 of -0.174 (4), 0.124 (5), -0.034 (3), 0.084 (5) and 0.063 (5) Å, respectively. The ring formed by atoms C10—C15 is also planar, with maxsimum deviation from the plane of this six-membered ring for C9, S1, O1, O2 and N3 of -0.011 (6), 0.014 (1), -0.572 (3), -0.504 (3) and 1.583 (3) Å, respectively.

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
N30.1744 (4)0.57097 (12)0.7688 (4)0.0524 (9)
S10.17024 (13)0.58506 (4)0.97230 (15)0.0570 (4)
C160.1172 (4)0.52604 (15)0.7027 (5)0.0558 (12)
H16A0.06600.52910.58250.067*
H16B0.03760.51480.77180.067*
O10.3072 (3)0.61314 (11)1.0258 (4)0.0711 (9)
O20.1472 (3)0.54316 (10)1.0634 (3)0.0705 (9)
C130.0001 (5)0.62020 (17)0.9733 (5)0.0499 (11)
C140.1448 (5)0.59988 (16)0.9922 (5)0.0630 (13)
H140.15250.56831.00430.076*
C150.2786 (5)0.6276 (2)0.9929 (6)0.0747 (15)
H150.37540.61421.00990.090*
C120.0092 (5)0.66656 (18)0.9483 (5)0.0629 (13)
H120.10590.68000.93170.075*
C110.1269 (6)0.69298 (16)0.9481 (6)0.0707 (14)
H110.12010.72450.93310.085*
C100.2723 (6)0.6739 (2)0.9694 (6)0.0704 (14)
N40.3811 (4)0.50627 (11)0.6138 (4)0.0507 (9)
C170.2535 (5)0.49152 (14)0.7104 (5)0.0581 (12)
H17A0.29810.48650.83180.070*
H17B0.21090.46260.66290.070*
C90.4191 (6)0.70290 (18)0.9696 (7)0.1034 (19)
H9A0.39260.73440.95210.155*
H9B0.45850.69971.07990.155*
H9C0.50010.69320.87680.155*
C190.5281 (5)0.48105 (16)0.6694 (5)0.0629 (13)
H19A0.51020.44870.64510.075*
H19B0.55840.48470.79470.075*
C180.3379 (5)0.50191 (16)0.4249 (5)0.0654 (13)
H18A0.24140.51940.38740.078*
H18B0.31570.47010.39510.078*
C10.2540 (5)0.71333 (17)0.2931 (6)0.0612 (13)
C50.0631 (5)0.62764 (15)0.5495 (5)0.0561 (12)
H50.03970.61850.56500.067*
C70.3473 (5)0.61942 (14)0.6173 (5)0.0533 (11)
H70.43630.60500.67880.064*
C40.0825 (5)0.66206 (15)0.4334 (5)0.0561 (12)
H40.00670.67630.37170.067*
C60.1943 (5)0.60637 (14)0.6437 (5)0.0492 (11)
C80.3673 (5)0.65378 (15)0.5000 (5)0.0503 (11)
C30.2351 (5)0.67563 (14)0.4081 (5)0.0495 (11)
N20.6579 (5)0.67289 (17)0.4519 (6)0.1083 (17)
C20.5289 (6)0.66511 (16)0.4722 (6)0.0701 (14)
N10.2653 (5)0.74369 (15)0.2050 (5)0.0854 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N30.058 (2)0.051 (3)0.051 (2)0.0012 (18)0.0150 (18)0.0000 (19)
S10.0441 (7)0.0751 (9)0.0512 (7)0.0030 (7)0.0047 (5)0.0086 (7)
C160.042 (3)0.063 (3)0.063 (3)0.005 (2)0.011 (2)0.011 (2)
O10.0432 (17)0.100 (3)0.068 (2)0.0126 (18)0.0010 (15)0.0051 (18)
O20.068 (2)0.086 (3)0.0582 (19)0.0062 (17)0.0116 (16)0.0308 (17)
C130.041 (3)0.068 (4)0.041 (2)0.001 (2)0.008 (2)0.001 (2)
C140.061 (3)0.062 (3)0.069 (3)0.003 (3)0.020 (2)0.014 (2)
C150.044 (3)0.092 (5)0.091 (4)0.005 (3)0.022 (3)0.010 (3)
C120.060 (3)0.059 (4)0.071 (3)0.011 (3)0.013 (2)0.003 (3)
C110.077 (4)0.052 (3)0.083 (4)0.004 (3)0.014 (3)0.004 (3)
C100.070 (4)0.072 (4)0.070 (3)0.011 (3)0.013 (3)0.001 (3)
N40.045 (2)0.061 (3)0.045 (2)0.0115 (18)0.0055 (18)0.0110 (18)
C170.059 (3)0.059 (3)0.057 (3)0.001 (2)0.011 (2)0.008 (2)
C90.082 (4)0.090 (5)0.140 (5)0.035 (3)0.021 (4)0.004 (4)
C190.058 (3)0.081 (4)0.049 (3)0.016 (3)0.008 (2)0.014 (2)
C180.050 (3)0.087 (4)0.058 (3)0.009 (3)0.003 (2)0.013 (3)
C10.066 (3)0.055 (4)0.061 (3)0.007 (3)0.001 (3)0.000 (3)
C50.041 (3)0.067 (3)0.060 (3)0.004 (2)0.009 (2)0.006 (3)
C70.047 (3)0.050 (3)0.064 (3)0.008 (2)0.012 (2)0.001 (2)
C40.056 (3)0.063 (3)0.049 (3)0.004 (2)0.002 (2)0.011 (2)
C60.056 (3)0.051 (3)0.043 (3)0.002 (2)0.015 (2)0.000 (2)
C80.051 (3)0.048 (3)0.054 (3)0.006 (2)0.016 (2)0.001 (2)
C30.060 (3)0.047 (3)0.043 (3)0.000 (2)0.010 (2)0.001 (2)
N20.062 (3)0.134 (5)0.132 (4)0.011 (3)0.023 (3)0.031 (3)
C20.066 (3)0.068 (4)0.077 (3)0.002 (3)0.014 (3)0.017 (3)
N10.102 (3)0.069 (3)0.081 (3)0.014 (3)0.001 (3)0.020 (2)
Geometric parameters (Å, º) top
N3—C61.440 (5)C17—H17B0.9700
N3—C161.465 (5)C9—H9A0.9600
N3—S11.628 (3)C9—H9B0.9600
S1—O11.429 (3)C9—H9C0.9600
S1—O21.438 (3)C19—C18i1.511 (5)
S1—C131.765 (4)C19—H19A0.9700
C16—C171.523 (5)C19—H19B0.9700
C16—H16A0.9700C18—C19i1.511 (5)
C16—H16B0.9700C18—H18A0.9700
C13—C121.372 (5)C18—H18B0.9700
C13—C141.382 (5)C1—N11.130 (5)
C14—C151.388 (6)C1—C31.437 (6)
C14—H140.9300C5—C41.372 (5)
C15—C101.368 (6)C5—C61.382 (5)
C15—H150.9300C5—H50.9300
C12—C111.382 (6)C7—C81.378 (5)
C12—H120.9300C7—C61.386 (5)
C11—C101.376 (6)C7—H70.9300
C11—H110.9300C4—C31.385 (5)
C10—C91.499 (6)C4—H40.9300
N4—C191.453 (4)C8—C31.389 (5)
N4—C171.456 (4)C8—C21.446 (6)
N4—C181.456 (5)N2—C21.142 (5)
C17—H17A0.9700
C6—N3—C16118.3 (3)C16—C17—H17B109.0
C6—N3—S1119.0 (3)H17A—C17—H17B107.8
C16—N3—S1120.8 (3)C10—C9—H9A109.5
O1—S1—O2120.41 (18)C10—C9—H9B109.5
O1—S1—N3107.37 (18)H9A—C9—H9B109.5
O2—S1—N3106.16 (18)C10—C9—H9C109.5
O1—S1—C13106.8 (2)H9A—C9—H9C109.5
O2—S1—C13109.1 (2)H9B—C9—H9C109.5
N3—S1—C13106.16 (17)N4—C19—C18i110.7 (3)
N3—C16—C17111.7 (3)N4—C19—H19A109.5
N3—C16—H16A109.3C18i—C19—H19A109.5
C17—C16—H16A109.3N4—C19—H19B109.5
N3—C16—H16B109.3C18i—C19—H19B109.5
C17—C16—H16B109.3H19A—C19—H19B108.1
H16A—C16—H16B107.9N4—C18—C19i110.7 (3)
C12—C13—C14120.5 (4)N4—C18—H18A109.5
C12—C13—S1120.7 (3)C19i—C18—H18A109.5
C14—C13—S1118.7 (4)N4—C18—H18B109.5
C13—C14—C15118.6 (4)C19i—C18—H18B109.5
C13—C14—H14120.7H18A—C18—H18B108.1
C15—C14—H14120.7N1—C1—C3177.9 (5)
C10—C15—C14122.0 (4)C4—C5—C6120.9 (4)
C10—C15—H15119.0C4—C5—H5119.6
C14—C15—H15119.0C6—C5—H5119.6
C13—C12—C11119.2 (4)C8—C7—C6119.9 (4)
C13—C12—H12120.4C8—C7—H7120.1
C11—C12—H12120.4C6—C7—H7120.1
C10—C11—C12121.7 (5)C5—C4—C3120.0 (4)
C10—C11—H11119.1C5—C4—H4120.0
C12—C11—H11119.1C3—C4—H4120.0
C15—C10—C11117.9 (4)C5—C6—C7119.4 (4)
C15—C10—C9120.8 (5)C5—C6—N3121.0 (4)
C11—C10—C9121.3 (5)C7—C6—N3119.6 (4)
C19—N4—C17111.0 (3)C7—C8—C3120.5 (4)
C19—N4—C18109.5 (3)C7—C8—C2117.9 (4)
C17—N4—C18112.8 (3)C3—C8—C2121.6 (4)
N4—C17—C16113.0 (3)C4—C3—C8119.3 (4)
N4—C17—H17A109.0C4—C3—C1119.4 (4)
C16—C17—H17A109.0C8—C3—C1121.2 (4)
N4—C17—H17B109.0N2—C2—C8178.1 (5)
C6—N3—S1—O150.7 (3)C19—N4—C17—C16161.3 (4)
C16—N3—S1—O1145.4 (3)C18—N4—C17—C1675.4 (4)
C6—N3—S1—O2179.3 (3)N3—C16—C17—N457.3 (5)
C16—N3—S1—O215.4 (3)C17—N4—C19—C18i177.2 (4)
C6—N3—S1—C1363.2 (3)C18—N4—C19—C18i57.6 (5)
C16—N3—S1—C13100.6 (3)C19—N4—C18—C19i57.6 (5)
C6—N3—C16—C17101.9 (4)C17—N4—C18—C19i178.3 (3)
S1—N3—C16—C1794.2 (4)C6—C5—C4—C30.6 (6)
O1—S1—C13—C1226.9 (4)C4—C5—C6—C71.4 (6)
O2—S1—C13—C12158.5 (3)C4—C5—C6—N3178.5 (4)
N3—S1—C13—C1287.4 (4)C8—C7—C6—C51.0 (6)
O1—S1—C13—C14155.8 (3)C8—C7—C6—N3178.9 (4)
O2—S1—C13—C1424.2 (4)C16—N3—C6—C572.7 (5)
N3—S1—C13—C1489.9 (3)S1—N3—C6—C591.5 (4)
C12—C13—C14—C152.7 (6)C16—N3—C6—C7107.4 (4)
S1—C13—C14—C15180.0 (3)S1—N3—C6—C788.4 (4)
C13—C14—C15—C102.3 (7)C6—C7—C8—C30.2 (6)
C14—C13—C12—C112.1 (6)C6—C7—C8—C2177.8 (4)
S1—C13—C12—C11179.3 (3)C5—C4—C3—C80.6 (6)
C13—C12—C11—C101.1 (7)C5—C4—C3—C1176.7 (4)
C14—C15—C10—C111.3 (7)C7—C8—C3—C41.0 (6)
C14—C15—C10—C9179.5 (5)C2—C8—C3—C4177.0 (4)
C12—C11—C10—C150.6 (7)C7—C8—C3—C1176.3 (4)
C12—C11—C10—C9179.8 (4)C2—C8—C3—C15.8 (6)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···N40.932.953.319 (5)105
C15—H15···O1ii0.932.693.559 (5)155
C18—H18A···O2iii0.972.603.248 (5)123
Symmetry codes: (ii) x1, y, z; (iii) x, y, z1.
 

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