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The title compound, C22H26N2O2S2, consists of a pentacyclic system containing a carbazolenine skeleton with an ethyl group, a methoxy­ethyl group and a di­thiol­ane ring as substituents. A few interatomic close contacts seem to influence the geometry of the carbazolenine core structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802004075/wn6085sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802004075/wn6085Isup2.hkl
Contains datablock I

CCDC reference: 183782

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.064
  • wR factor = 0.217
  • Data-to-parameter ratio = 15.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
DIFMX_01 Alert C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 1.350 Test value = 1.200 DIFMX_02 Alert C The minimum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I) top
Crystal data top
C22H26N2O2S2F(000) = 880
Mr = 414.57Dx = 1.389 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 8.6833 (10) Åθ = 10–15°
b = 22.975 (2) ŵ = 0.29 mm1
c = 9.9726 (10) ÅT = 293 K
β = 94.675 (10)°Prism, colorless
V = 1982.9 (3) Å30.3 × 0.2 × 0.1 mm
Z = 4
Data collection top
Enraf-Nonius TurboCAD4
diffractometer
3067 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.013
Graphite monochromatorθmax = 26.3°, θmin = 2.2°
non–profiled ω scansh = 010
Absorption correction: ψ scan
(North et al., 1968)
k = 028
Tmin = 0.933, Tmax = 0.971l = 1212
4283 measured reflections3 standard reflections every 120 min
4016 independent reflections intensity decay: 1%
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)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.217H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.122P)2 + 2.1074P]
where P = (Fo2 + 2Fc2)/3
4016 reflections(Δ/σ)max = 0.021
254 parametersΔρmax = 1.35 e Å3
0 restraintsΔρmin = 0.80 e Å3
Special details top

Experimental. Number of psi-scan sets used was 7. Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied.

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
S20.18602 (13)0.17768 (4)0.59845 (10)0.0585 (3)
S10.01229 (11)0.25138 (4)0.41098 (9)0.0493 (3)
C40.2707 (3)0.30933 (10)0.3418 (2)0.0221 (5)
H4A0.16640.30550.29460.026*
H4B0.34530.31290.27230.026*
O170.4560 (3)0.43025 (12)0.3194 (3)0.0581 (7)
C11A0.2708 (4)0.39032 (14)0.6737 (3)0.0377 (7)
N70.1105 (3)0.30998 (12)0.7077 (3)0.0440 (7)
N20.5365 (3)0.36708 (13)0.4878 (3)0.0459 (7)
C11B0.3002 (4)0.34527 (13)0.5709 (3)0.0366 (7)
C6A0.1875 (4)0.29908 (14)0.6056 (3)0.0377 (7)
C20.4315 (4)0.39194 (15)0.4011 (3)0.0438 (7)
O150.7182 (4)0.40345 (13)0.7268 (3)0.0671 (8)
C110.3303 (4)0.44545 (15)0.7011 (3)0.0464 (8)
H110.40530.46190.64810.056*
C7A0.1597 (4)0.36693 (14)0.7524 (3)0.0410 (7)
C30.2755 (4)0.36270 (14)0.4212 (3)0.0387 (7)
C180.1330 (4)0.39887 (15)0.3815 (3)0.0465 (8)
H18A0.15100.43910.41480.056*
H18B0.04500.38280.42660.056*
C120.4603 (4)0.26266 (15)0.4993 (4)0.0485 (8)
H12A0.54500.25930.43900.058*
H12B0.47250.23120.56700.058*
C10.4683 (4)0.32221 (14)0.5699 (3)0.0419 (7)
H10.52140.31990.66260.050*
C60.1739 (4)0.24797 (14)0.5113 (3)0.0410 (7)
C50.3054 (4)0.25669 (14)0.4181 (3)0.0443 (8)
H50.30860.22290.35530.053*
C80.1077 (4)0.39705 (17)0.8590 (3)0.0503 (8)
H80.03280.38070.91230.060*
C100.2770 (5)0.47603 (17)0.8086 (4)0.0539 (9)
H100.31590.51390.82910.065*
C90.1683 (5)0.45201 (17)0.8860 (4)0.0549 (9)
H90.13430.47360.95930.066*
C130.7022 (4)0.37921 (19)0.4956 (4)0.0593 (10)
H13A0.73070.39270.40670.071*
H13B0.75990.34290.51800.071*
C140.7484 (5)0.4247 (2)0.5998 (5)0.0646 (11)
H14A0.85980.43370.59840.077*
H14B0.68910.46090.58000.077*
C190.0892 (5)0.4010 (2)0.2305 (4)0.0652 (11)
H19A0.00300.42530.21260.098*
H19B0.06740.36150.19690.098*
H19C0.17480.41760.18490.098*
C200.1091 (5)0.2042 (2)0.5201 (4)0.0614 (10)
H20A0.12470.22420.60590.074*
H20B0.21120.19250.47710.074*
C160.7336 (6)0.4474 (2)0.8261 (5)0.0751 (13)
H16A0.71270.43100.91350.113*
H16B0.65980.47880.80240.113*
H16C0.83890.46300.83140.113*
C210.0073 (6)0.15206 (19)0.5448 (5)0.0681 (12)
H21A0.00540.12880.46140.082*
H21B0.04700.12720.61540.082*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S20.0733 (7)0.0402 (5)0.0603 (6)0.0045 (4)0.0042 (5)0.0088 (4)
S10.0525 (6)0.0527 (5)0.0417 (5)0.0034 (4)0.0029 (4)0.0030 (4)
C40.0307 (13)0.0225 (12)0.0136 (10)0.0003 (10)0.0052 (9)0.0019 (9)
O170.0631 (16)0.0572 (16)0.0556 (15)0.0089 (13)0.0144 (12)0.0129 (12)
C11A0.0387 (16)0.0407 (16)0.0337 (15)0.0030 (13)0.0028 (12)0.0009 (12)
N70.0487 (16)0.0448 (15)0.0395 (14)0.0048 (12)0.0087 (12)0.0004 (12)
N20.0385 (15)0.0517 (17)0.0486 (16)0.0016 (12)0.0098 (12)0.0010 (13)
C11B0.0399 (16)0.0376 (16)0.0328 (15)0.0003 (13)0.0055 (12)0.0003 (12)
C6A0.0422 (17)0.0389 (16)0.0316 (14)0.0005 (13)0.0010 (12)0.0015 (12)
C20.0467 (18)0.0451 (18)0.0411 (17)0.0029 (14)0.0121 (14)0.0035 (14)
O150.0696 (19)0.0618 (18)0.0690 (19)0.0140 (14)0.0006 (15)0.0038 (14)
C110.0493 (19)0.0445 (18)0.0459 (18)0.0053 (15)0.0062 (15)0.0046 (14)
C7A0.0448 (18)0.0439 (18)0.0345 (15)0.0015 (14)0.0044 (13)0.0001 (13)
C30.0455 (18)0.0380 (16)0.0333 (15)0.0010 (13)0.0065 (13)0.0020 (12)
C180.0461 (18)0.0431 (18)0.0501 (19)0.0034 (14)0.0027 (15)0.0059 (15)
C120.0471 (19)0.0461 (19)0.053 (2)0.0101 (15)0.0090 (16)0.0001 (15)
C10.0410 (17)0.0446 (18)0.0403 (16)0.0023 (13)0.0050 (13)0.0026 (13)
C60.0482 (18)0.0366 (16)0.0378 (16)0.0015 (13)0.0015 (14)0.0005 (13)
C50.055 (2)0.0378 (17)0.0414 (17)0.0027 (14)0.0090 (15)0.0056 (13)
C80.055 (2)0.057 (2)0.0400 (17)0.0028 (17)0.0115 (15)0.0037 (15)
C100.060 (2)0.0457 (19)0.056 (2)0.0018 (16)0.0020 (17)0.0112 (16)
C90.064 (2)0.056 (2)0.0454 (19)0.0070 (18)0.0103 (17)0.0129 (16)
C130.0387 (19)0.069 (3)0.072 (3)0.0016 (17)0.0166 (17)0.002 (2)
C140.049 (2)0.064 (3)0.079 (3)0.0126 (19)0.000 (2)0.006 (2)
C190.071 (3)0.068 (3)0.054 (2)0.004 (2)0.013 (2)0.006 (2)
C200.058 (2)0.071 (3)0.056 (2)0.012 (2)0.0081 (18)0.005 (2)
C160.069 (3)0.073 (3)0.081 (3)0.005 (2)0.007 (2)0.017 (2)
C210.081 (3)0.056 (2)0.067 (3)0.021 (2)0.006 (2)0.006 (2)
Geometric parameters (Å, º) top
S2—C211.818 (5)C18—H18B0.9900
S2—C61.833 (3)C12—C51.518 (5)
S1—C201.793 (4)C12—C11.538 (5)
S1—C61.832 (3)C12—H12A0.9900
C4—C51.447 (4)C12—H12B0.9900
C4—C31.459 (4)C1—H11.0000
C4—H4A0.9900C6—C51.543 (5)
C4—H4B0.9900C5—H51.0000
O17—C21.230 (4)C8—C91.386 (5)
C11A—C111.387 (5)C8—H80.9500
C11A—C7A1.399 (4)C10—C91.382 (6)
C11A—C11B1.493 (4)C10—H100.9500
N7—C6A1.287 (4)C9—H90.9500
N7—C7A1.436 (4)C13—C141.505 (6)
N2—C21.332 (5)C13—H13A0.9900
N2—C131.462 (4)C13—H13B0.9900
N2—C11.471 (4)C14—H14A0.9900
C11B—C6A1.503 (4)C14—H14B0.9900
C11B—C31.543 (4)C19—H19A0.9800
C11B—C11.553 (4)C19—H19B0.9800
C6A—C61.504 (4)C19—H19C0.9800
C2—C31.539 (4)C20—C211.498 (7)
O15—C141.402 (5)C20—H20A0.9900
O15—C161.413 (5)C20—H20B0.9900
C11—C101.392 (5)C16—H16A0.9800
C11—H110.9500C16—H16B0.9800
C7A—C81.375 (5)C16—H16C0.9800
C3—C181.516 (5)C21—H21A0.9900
C18—C191.524 (5)C21—H21B0.9900
C18—H18A0.9900
C21—S2—C697.44 (18)C6A—C6—C5104.5 (3)
C20—S1—C694.55 (18)C6A—C6—S1109.2 (2)
C5—C4—C3114.9 (2)C5—C6—S1109.2 (2)
C5—C4—H4A108.5C6A—C6—S2113.1 (2)
C3—C4—H4A108.5C5—C6—S2112.5 (2)
C5—C4—H4B108.5S1—C6—S2108.11 (17)
C3—C4—H4B108.5C4—C5—C12110.0 (3)
H4A—C4—H4B107.5C4—C5—C6107.0 (3)
C11—C11A—C7A120.2 (3)C12—C5—C6110.9 (3)
C11—C11A—C11B133.4 (3)C4—C5—H5109.6
C7A—C11A—C11B106.4 (3)C12—C5—H5109.6
C6A—N7—C7A105.2 (3)C6—C5—H5109.6
C2—N2—C13124.8 (3)C7A—C8—C9117.7 (3)
C2—N2—C1112.1 (3)C7A—C8—H8121.1
C13—N2—C1122.9 (3)C9—C8—H8121.1
C11A—C11B—C6A100.4 (2)C9—C10—C11120.9 (3)
C11A—C11B—C3117.8 (3)C9—C10—H10119.6
C6A—C11B—C3111.4 (2)C11—C10—H10119.6
C11A—C11B—C1117.0 (3)C10—C9—C8121.4 (3)
C6A—C11B—C1113.0 (3)C10—C9—H9119.3
C3—C11B—C198.0 (2)C8—C9—H9119.3
N7—C6A—C11B115.8 (3)N2—C13—C14112.0 (3)
N7—C6A—C6128.9 (3)N2—C13—H13A109.2
C11B—C6A—C6115.3 (3)C14—C13—H13A109.2
O17—C2—N2126.2 (3)N2—C13—H13B109.2
O17—C2—C3126.9 (3)C14—C13—H13B109.2
N2—C2—C3106.9 (3)H13A—C13—H13B107.9
C14—O15—C16111.7 (4)O15—C14—C13108.8 (3)
C11A—C11—C10118.1 (3)O15—C14—H14A109.9
C11A—C11—H11121.0C13—C14—H14A109.9
C10—C11—H11121.0O15—C14—H14B109.9
C8—C7A—C11A121.7 (3)C13—C14—H14B109.9
C8—C7A—N7126.1 (3)H14A—C14—H14B108.3
C11A—C7A—N7112.2 (3)C18—C19—H19A109.5
C4—C3—C18109.4 (3)C18—C19—H19B109.5
C4—C3—C2106.4 (2)H19A—C19—H19B109.5
C18—C3—C2115.8 (3)C18—C19—H19C109.5
C4—C3—C11B107.6 (2)H19A—C19—H19C109.5
C18—C3—C11B116.2 (3)H19B—C19—H19C109.5
C2—C3—C11B100.6 (3)C21—C20—S1106.5 (3)
C3—C18—C19114.1 (3)C21—C20—H20A110.4
C3—C18—H18A108.7S1—C20—H20A110.4
C19—C18—H18A108.7C21—C20—H20B110.4
C3—C18—H18B108.7S1—C20—H20B110.4
C19—C18—H18B108.7H20A—C20—H20B108.6
H18A—C18—H18B107.6O15—C16—H16A109.5
C5—C12—C1109.2 (3)O15—C16—H16B109.5
C5—C12—H12A109.8H16A—C16—H16B109.5
C1—C12—H12A109.8O15—C16—H16C109.5
C5—C12—H12B109.8H16A—C16—H16C109.5
C1—C12—H12B109.8H16B—C16—H16C109.5
H12A—C12—H12B108.3C20—C21—S2107.9 (3)
N2—C1—C12111.9 (3)C20—C21—H21A110.1
N2—C1—C11B100.7 (2)S2—C21—H21A110.1
C12—C1—C11B107.4 (3)C20—C21—H21B110.1
N2—C1—H1112.1S2—C21—H21B110.1
C12—C1—H1112.1H21A—C21—H21B108.4
C11B—C1—H1112.1
C11—C11A—C11B—C6A178.5 (3)C2—N2—C1—C1286.0 (3)
C7A—C11A—C11B—C6A2.0 (3)C13—N2—C1—C1289.9 (4)
C11—C11A—C11B—C357.4 (5)C2—N2—C1—C11B27.8 (3)
C7A—C11A—C11B—C3123.0 (3)C13—N2—C1—C11B156.3 (3)
C11—C11A—C11B—C159.0 (5)C5—C12—C1—N291.5 (3)
C7A—C11A—C11B—C1120.6 (3)C5—C12—C1—C11B18.1 (4)
C7A—N7—C6A—C11B1.8 (4)C11A—C11B—C1—N284.2 (3)
C7A—N7—C6A—C6174.3 (3)C6A—C11B—C1—N2160.0 (3)
C11A—C11B—C6A—N72.5 (4)C3—C11B—C1—N242.6 (3)
C3—C11B—C6A—N7127.9 (3)C11A—C11B—C1—C12158.6 (3)
C1—C11B—C6A—N7122.9 (3)C6A—C11B—C1—C1242.8 (3)
C11A—C11B—C6A—C6174.2 (3)C3—C11B—C1—C1274.6 (3)
C3—C11B—C6A—C648.7 (4)N7—C6A—C6—C5175.2 (3)
C1—C11B—C6A—C660.5 (3)C11B—C6A—C6—C58.7 (4)
C13—N2—C2—O173.4 (6)N7—C6A—C6—S168.0 (4)
C1—N2—C2—O17179.3 (3)C11B—C6A—C6—S1108.1 (3)
C13—N2—C2—C3175.5 (3)N7—C6A—C6—S252.5 (4)
C1—N2—C2—C30.4 (4)C11B—C6A—C6—S2131.4 (2)
C7A—C11A—C11—C100.4 (5)C20—S1—C6—C6A95.0 (3)
C11B—C11A—C11—C10179.1 (3)C20—S1—C6—C5151.2 (2)
C11—C11A—C7A—C80.7 (5)C20—S1—C6—S228.4 (2)
C11B—C11A—C7A—C8178.9 (3)C21—S2—C6—C6A116.7 (3)
C11—C11A—C7A—N7179.2 (3)C21—S2—C6—C5125.1 (3)
C11B—C11A—C7A—N71.2 (4)C21—S2—C6—S14.4 (2)
C6A—N7—C7A—C8179.6 (3)C3—C4—C5—C1254.5 (3)
C6A—N7—C7A—C11A0.3 (4)C3—C4—C5—C666.1 (3)
C5—C4—C3—C18133.2 (3)C1—C12—C5—C446.1 (4)
C5—C4—C3—C2101.0 (3)C1—C12—C5—C672.2 (3)
C5—C4—C3—C11B6.2 (4)C6A—C6—C5—C464.8 (3)
O17—C2—C3—C495.3 (4)S1—C6—C5—C452.0 (3)
N2—C2—C3—C483.6 (3)S2—C6—C5—C4172.1 (2)
O17—C2—C3—C1826.5 (5)C6A—C6—C5—C1255.2 (3)
N2—C2—C3—C18154.6 (3)S1—C6—C5—C12172.0 (2)
O17—C2—C3—C11B152.6 (3)S2—C6—C5—C1267.9 (3)
N2—C2—C3—C11B28.5 (3)C11A—C7A—C8—C90.4 (5)
C11A—C11B—C3—C4165.2 (3)N7—C7A—C8—C9179.4 (3)
C6A—C11B—C3—C450.1 (3)C11A—C11—C10—C90.2 (6)
C1—C11B—C3—C468.4 (3)C11—C10—C9—C80.5 (6)
C11A—C11B—C3—C1842.3 (4)C7A—C8—C9—C100.2 (6)
C6A—C11B—C3—C1872.9 (4)C2—N2—C13—C1494.9 (4)
C1—C11B—C3—C18168.6 (3)C1—N2—C13—C1489.6 (4)
C11A—C11B—C3—C283.6 (3)C16—O15—C14—C13169.8 (4)
C6A—C11B—C3—C2161.3 (3)N2—C13—C14—O1563.2 (5)
C1—C11B—C3—C242.8 (3)C6—S1—C20—C2148.8 (3)
C4—C3—C18—C1942.1 (4)S1—C20—C21—S251.2 (3)
C2—C3—C18—C1978.1 (4)C6—S2—C21—C2027.9 (3)
C11B—C3—C18—C19164.1 (3)
Table 2. Comparison of the bond angles (°) in the carbazole core of (I) with the corresponding values in the related compounds (II), (III), (IV), (V) and (VI). top
Angles(I)(II)(III)(IV)(V)(VI)
C6-C6a-N7128.9 (3)125.0 (3)124.1 (7)126.4 (2)127.5 (2)126.7 (2)
C11b-C11a-C11133.4 (2)133.6 (4)136.3 (8)134.7 (2)134.0 (3)134.7 (2)
N7-C7a-C8126.1 (3)130.8 (4)128.1 (9)129.8 (2)129.4 (3)129.1 (2)
S1-C6-C6a109.2 (2)110.2 (3)112.1 (5)112.8 (1)115.9 (1)115.9 (2)
C6a-N7-C7a105.2 (3)108.6 (3)108.1 (6)109.6 (1)108.1 (1)108.1 (2)
 

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