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The crystal structure of the title mol­ecule, C19H18N2O6S, confirms the structure of this novel Diels-Alder adduct formed from the reaction of 3-nitro-1-(phenyl­sulfon­yl)indole and 1-meth­oxy-3-(trimethyl­siloxy)-1,3-butadiene (Danishefsky's diene). The angle between the planes of the indoline ring system and the phenyl­sulfonyl ring is 69.9 (4)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807017448/tk2148sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807017448/tk2148Isup2.hkl
Contains datablock I

CCDC reference: 647459

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.015 Å
  • R factor = 0.055
  • wR factor = 0.255
  • Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.75
Author Response: ...Data collected on an old Rigaku AFC6s Diffractometer
PLAT026_ALERT_3_A Ratio Observed / Unique Reflections too Low ....         23 Perc.
Author Response: ...Data collected on an old Rigaku AFC6s Diffractometer
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.80
Author Response: ...Data collected on an old Rigaku AFC6s Diffractometer

Alert level B PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 15
Alert level C RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.255 PLAT030_ALERT_1_C _diffrn_reflns_number .LE. _reflns_number_total ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2
Alert level G REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 3333 From the CIF: _diffrn_reflns_limit_ max hkl 30. 16. 0. From the CIF: _diffrn_reflns_limit_ min hkl 0. 0. -14. TEST1: Expected hkl limits for theta max Calculated maximum hkl 30. 19. 14. Calculated minimum hkl -30. -19. -14.
3 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: CrystalStructure (Rigaku/MSC, 2005); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

4-Methoxy-4a-nitro-9-(phenylsulfonyl)-4,4a,9,9a-tetrahydro-1H-carbazol-2(3H)-one top
Crystal data top
C19H18N2O6SF(000) = 1680
Mr = 402.41Dx = 1.386 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ac 2abCell parameters from 17 reflections
a = 23.352 (6) Åθ = 6.2–11.8°
b = 15.085 (14) ŵ = 0.21 mm1
c = 10.952 (9) ÅT = 296 K
V = 3858 (5) Å3Prism, colourless
Z = 80.40 × 0.40 × 0.20 mm
Data collection top
Rigaku AFC-6S
diffractometer
780 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 27.5°, θmin = 1.7°
ω/2θ scansh = 030
Absorption correction: ψ scan
(North et al., 1968)
k = 016
Tmin = 0.922, Tmax = 0.960l = 140
3333 measured reflections3 standard reflections every 150 reflections
3333 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.255 w = 1/[σ2(Fo2) + (0.0932P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.93(Δ/σ)max < 0.001
3333 reflectionsΔρmax = 0.33 e Å3
255 parametersΔρmin = 0.26 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0038 (7)
Special details top

Experimental. IR (film): νmax 1722 (CO), 1361 (SO2), 1166 (SO2) cm-1; UV (EtOH): λmax 256 nm; 1H (CD2Cl2, δ, p.p.m.): 7.73–7.80 (m, 3H), 7.55–7.62 (m, 2H), 7.42–7.52 (m, 3H), 7.15–7.20 (m, 1H), 5.70 (dd, 1H, J= 2.2 and 6.2 Hz), 4.67 (m, 1H), 3.46 (s, 3H), 3.20 (dd, 1H, J= 6.2 and 16.5 Hz), 3.15 (dd, 1H, J= 2.2 and 16.5 Hz), 2.67 (dd, 1H, J = 3 and 19 Hz), 1.92 (dd, 1H, J = 3 and 19 Hz); 13C (CD2Cl2, δ, p.p.m.): 204.2, 142.7, 136.2, 134.4, 133.5, 129.6, 127.9, 125.9, 125.6, 125.4, 116.8, 96.1, 20.5, 62.0, 58.3, 44.5, 37.7.

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
S10.84061 (10)0.18198 (15)0.7413 (3)0.0505 (7)
O10.7979 (2)0.1863 (4)0.8320 (6)0.0639 (19)
O20.8441 (2)0.2496 (4)0.6501 (5)0.0641 (18)
O30.6950 (3)0.0144 (5)0.5633 (8)0.105 (3)
O40.8504 (3)0.2176 (4)0.6132 (7)0.078 (2)
O50.9466 (3)0.0745 (6)0.7608 (9)0.129 (4)
O60.8836 (4)0.1376 (7)0.8624 (9)0.123 (4)
N10.8284 (3)0.0872 (5)0.6691 (7)0.048 (2)
N20.9004 (5)0.0946 (6)0.7770 (9)0.076 (3)
C10.7518 (4)0.0115 (6)0.7442 (9)0.055 (2)
H10.74200.05400.80730.066*
H20.73110.04300.76080.066*
C20.7336 (4)0.0473 (7)0.6216 (10)0.058 (3)
C30.7670 (4)0.1256 (6)0.5786 (9)0.065 (3)
H30.78260.11250.49850.077*
H40.74120.17560.57000.077*
C40.8157 (4)0.1517 (6)0.6628 (10)0.058 (3)
H50.79990.17260.74060.070*
C50.8526 (4)0.0681 (6)0.6859 (8)0.050 (2)
C60.8793 (4)0.0282 (6)0.5757 (10)0.054 (3)
C70.9114 (5)0.0654 (8)0.4831 (11)0.089 (4)
H60.92090.12520.48530.107*
C80.9291 (6)0.0137 (9)0.3883 (12)0.112 (5)
H70.95250.03850.32880.135*
C90.9134 (6)0.0745 (9)0.3776 (11)0.105 (5)
H80.92490.10740.31010.126*
C100.8808 (5)0.1126 (7)0.4671 (10)0.079 (4)
H90.87030.17190.46100.095*
C110.8634 (4)0.0624 (7)0.5677 (9)0.055 (3)
C120.8161 (3)0.0068 (6)0.7482 (9)0.051 (2)
H180.82890.01690.83230.061*
C130.9083 (4)0.1725 (6)0.8130 (9)0.046 (2)
C140.9130 (4)0.1361 (6)0.9278 (10)0.064 (3)
H100.88050.11760.96950.077*
C150.9655 (5)0.1274 (8)0.9799 (10)0.081 (4)
H110.96920.10151.05660.097*
C161.0124 (5)0.1566 (9)0.9195 (13)0.098 (4)
H121.04810.15120.95610.117*
C171.0085 (4)0.1943 (8)0.8049 (12)0.085 (4)
H131.04130.21520.76600.102*
C180.9562 (4)0.2009 (6)0.7487 (10)0.064 (3)
H140.95290.22370.67010.077*
C190.8266 (5)0.3045 (6)0.6299 (13)0.115 (5)
H150.84060.32920.70500.138*
H160.83780.34180.56310.138*
H170.78560.30050.63280.138*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0505 (14)0.0443 (13)0.0566 (16)0.0007 (13)0.0009 (16)0.0043 (17)
O10.058 (4)0.061 (4)0.072 (5)0.004 (4)0.007 (4)0.013 (4)
O20.080 (4)0.043 (3)0.070 (4)0.006 (4)0.006 (4)0.013 (4)
O30.093 (6)0.086 (6)0.135 (8)0.011 (5)0.059 (6)0.004 (5)
O40.065 (4)0.040 (4)0.129 (7)0.007 (4)0.029 (4)0.006 (4)
O50.049 (5)0.188 (10)0.150 (8)0.015 (5)0.015 (7)0.045 (8)
O60.100 (7)0.175 (10)0.095 (7)0.008 (6)0.021 (6)0.052 (7)
N10.055 (5)0.048 (5)0.041 (5)0.006 (4)0.001 (4)0.006 (4)
N20.080 (7)0.073 (6)0.075 (8)0.007 (6)0.007 (8)0.016 (6)
C10.054 (5)0.046 (6)0.064 (6)0.008 (4)0.002 (7)0.007 (7)
C20.045 (7)0.049 (7)0.080 (9)0.014 (6)0.007 (6)0.006 (6)
C30.064 (7)0.063 (7)0.066 (8)0.026 (6)0.003 (6)0.002 (6)
C40.049 (6)0.049 (6)0.077 (7)0.007 (5)0.003 (6)0.009 (6)
C50.056 (6)0.044 (6)0.050 (6)0.004 (5)0.006 (6)0.001 (5)
C60.049 (6)0.049 (7)0.063 (7)0.020 (5)0.010 (5)0.002 (6)
C70.104 (9)0.077 (9)0.085 (9)0.012 (8)0.060 (8)0.013 (7)
C80.153 (13)0.074 (9)0.110 (11)0.019 (9)0.085 (10)0.014 (9)
C90.163 (13)0.084 (10)0.069 (9)0.031 (10)0.065 (9)0.024 (8)
C100.131 (11)0.044 (7)0.061 (8)0.035 (7)0.031 (8)0.001 (7)
C110.047 (6)0.063 (7)0.055 (7)0.010 (6)0.006 (6)0.001 (6)
C120.054 (5)0.058 (6)0.041 (5)0.008 (5)0.016 (6)0.002 (6)
C130.047 (6)0.041 (5)0.049 (6)0.001 (5)0.003 (5)0.013 (5)
C140.058 (7)0.070 (7)0.064 (8)0.002 (6)0.004 (7)0.007 (6)
C150.056 (7)0.121 (11)0.067 (8)0.017 (8)0.019 (7)0.008 (7)
C160.054 (8)0.133 (13)0.105 (12)0.017 (8)0.020 (9)0.021 (10)
C170.047 (7)0.104 (10)0.104 (11)0.012 (7)0.007 (7)0.017 (8)
C180.047 (6)0.069 (7)0.076 (7)0.009 (5)0.005 (7)0.002 (7)
C190.102 (9)0.041 (7)0.203 (15)0.020 (7)0.047 (9)0.000 (8)
Geometric parameters (Å, º) top
S1—O11.409 (6)C6—C111.419 (12)
S1—O21.431 (6)C7—C81.362 (14)
S1—N11.659 (7)C7—H60.9300
S1—C131.772 (9)C8—C91.384 (15)
O3—C21.210 (10)C8—H70.9300
O4—C41.393 (10)C9—C101.368 (13)
O4—C191.435 (10)C9—H80.9300
O5—N21.134 (10)C10—C111.398 (12)
O6—N21.205 (10)C10—H90.9300
N1—C111.428 (11)C12—H180.9800
N1—C121.518 (10)C13—C141.376 (12)
N2—C51.550 (13)C13—C181.389 (11)
C1—C21.509 (12)C14—C151.358 (12)
C1—C121.529 (11)C14—H100.9300
C1—H10.9700C15—C161.353 (14)
C1—H20.9700C15—H110.9300
C2—C31.492 (12)C16—C171.381 (14)
C3—C41.517 (12)C16—H120.9300
C3—H30.9700C17—C181.372 (12)
C3—H40.9700C17—H130.9300
C4—C51.548 (11)C18—H140.9300
C4—H50.9800C19—H150.9600
C5—C61.486 (12)C19—H160.9600
C5—C121.571 (11)C19—H170.9600
C6—C71.380 (12)
O1—S1—O2120.0 (4)C8—C7—H6120.3
O1—S1—N1104.8 (4)C6—C7—H6120.3
O2—S1—N1107.0 (4)C7—C8—C9122.3 (11)
O1—S1—C13108.8 (4)C7—C8—H7118.8
O2—S1—C13108.5 (4)C9—C8—H7118.8
N1—S1—C13107.2 (4)C10—C9—C8119.3 (11)
C4—O4—C19112.1 (7)C10—C9—H8120.3
C11—N1—C12110.0 (7)C8—C9—H8120.3
C11—N1—S1119.9 (6)C9—C10—C11119.9 (10)
C12—N1—S1116.7 (6)C9—C10—H9120.0
O5—N2—O6125.1 (12)C11—C10—H9120.0
O5—N2—C5121.1 (10)C10—C11—C6119.6 (10)
O6—N2—C5113.8 (10)C10—C11—N1129.5 (10)
C2—C1—C12111.5 (8)C6—C11—N1110.8 (9)
C2—C1—H1109.3N1—C12—C1108.3 (7)
C12—C1—H1109.3N1—C12—C5103.0 (7)
C2—C1—H2109.3C1—C12—C5113.0 (7)
C12—C1—H2109.3N1—C12—H18110.8
H1—C1—H2108.0C1—C12—H18110.8
O3—C2—C3123.3 (10)C5—C12—H18110.8
O3—C2—C1122.1 (10)C14—C13—C18121.5 (9)
C3—C2—C1114.7 (9)C14—C13—S1120.6 (8)
C2—C3—C4114.0 (9)C18—C13—S1117.9 (8)
C2—C3—H3108.8C15—C14—C13119.7 (10)
C4—C3—H3108.8C15—C14—H10120.2
C2—C3—H4108.8C13—C14—H10120.2
C4—C3—H4108.8C16—C15—C14119.5 (11)
H3—C3—H4107.7C16—C15—H11120.2
O4—C4—C3112.6 (9)C14—C15—H11120.2
O4—C4—C5108.7 (7)C15—C16—C17121.8 (11)
C3—C4—C5107.7 (8)C15—C16—H12119.1
O4—C4—H5109.2C17—C16—H12119.1
C3—C4—H5109.2C18—C17—C16119.7 (11)
C5—C4—H5109.2C18—C17—H13120.2
C6—C5—C4115.5 (8)C16—C17—H13120.2
C6—C5—N2108.9 (8)C17—C18—C13117.8 (10)
C4—C5—N2107.2 (8)C17—C18—H14121.1
C6—C5—C12106.8 (8)C13—C18—H14121.1
C4—C5—C12110.8 (8)O4—C19—H15109.5
N2—C5—C12107.2 (7)O4—C19—H16109.5
C7—C6—C11119.2 (10)H15—C19—H16109.5
C7—C6—C5131.3 (9)O4—C19—H17109.5
C11—C6—C5109.3 (9)H15—C19—H17109.5
C8—C7—C6119.4 (11)H16—C19—H17109.5
O1—S1—N1—C11178.3 (6)C9—C10—C11—C60.5 (15)
O2—S1—N1—C1150.0 (7)C9—C10—C11—N1178.1 (10)
C13—S1—N1—C1166.2 (8)C7—C6—C11—C100.5 (14)
O1—S1—N1—C1244.7 (7)C5—C6—C11—C10176.3 (9)
O2—S1—N1—C12173.1 (6)C7—C6—C11—N1177.5 (8)
C13—S1—N1—C1270.8 (7)C5—C6—C11—N11.7 (10)
C12—C1—C2—O3127.3 (10)C12—N1—C11—C10173.8 (9)
C12—C1—C2—C352.4 (10)S1—N1—C11—C1046.6 (12)
O3—C2—C3—C4176.3 (9)C12—N1—C11—C63.9 (9)
C1—C2—C3—C43.4 (11)S1—N1—C11—C6135.6 (7)
C19—O4—C4—C382.0 (11)C11—N1—C12—C1115.6 (8)
C19—O4—C4—C5158.8 (9)S1—N1—C12—C1103.4 (7)
C2—C3—C4—O4172.5 (7)C11—N1—C12—C54.3 (8)
C2—C3—C4—C552.6 (11)S1—N1—C12—C5136.7 (6)
O4—C4—C5—C661.3 (11)C2—C1—C12—N171.3 (9)
C3—C4—C5—C661.0 (11)C2—C1—C12—C542.1 (10)
O4—C4—C5—N260.4 (10)C6—C5—C12—N13.2 (9)
C3—C4—C5—N2177.3 (8)C4—C5—C12—N1129.8 (8)
O4—C4—C5—C12177.1 (8)N2—C5—C12—N1113.4 (8)
C3—C4—C5—C1260.6 (10)C6—C5—C12—C1113.4 (8)
O5—N2—C5—C68.3 (13)C4—C5—C12—C113.3 (11)
O6—N2—C5—C6171.1 (9)N2—C5—C12—C1130.0 (8)
O5—N2—C5—C4134.0 (11)O1—S1—C13—C1425.9 (8)
O6—N2—C5—C445.5 (12)O2—S1—C13—C14157.9 (7)
O5—N2—C5—C12106.9 (12)N1—S1—C13—C1486.9 (8)
O6—N2—C5—C1273.6 (11)O1—S1—C13—C18155.6 (7)
C4—C5—C6—C750.2 (15)O2—S1—C13—C1823.5 (8)
N2—C5—C6—C770.5 (12)N1—S1—C13—C1891.6 (8)
C12—C5—C6—C7174.0 (10)C18—C13—C14—C150.1 (15)
C4—C5—C6—C11124.9 (9)S1—C13—C14—C15178.3 (8)
N2—C5—C6—C11114.4 (8)C13—C14—C15—C161.6 (16)
C12—C5—C6—C111.1 (10)C14—C15—C16—C170.8 (19)
C11—C6—C7—C82.5 (16)C15—C16—C17—C181.5 (19)
C5—C6—C7—C8177.3 (11)C16—C17—C18—C132.9 (16)
C6—C7—C8—C94 (2)C14—C13—C18—C172.1 (14)
C7—C8—C9—C103 (2)S1—C13—C18—C17179.4 (8)
C8—C9—C10—C110.4 (19)
 

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