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Vilsmeier formyl­ation of trans-1-(4-methyl­phenyl­sulfonyl)-2,5-bis(pyrrol-2-yl)­pyrrolidine leads to cleavage of the central ring then a reclosure resulting in the formation of trans-N-[2-formyl-4-(5-formyl­pyrrol-2-yl)-4,5,6,7-tetra­hydro­indol-7-yl]­toluene­sulfon­amide, C21H21N3O4S.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100003541/gd1093sup1.cif
Contains datablocks S607, (2)

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100003541/gd10932sup2.hkl
Contains datablock 2

CCDC reference: 146069

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1995); program(s) used to solve structure: SIR92 (Altomare et al. 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: TEXSAN.

(2) top
Crystal data top
C21H21N3O4SF(000) = 864
Mr = 411.47Dx = 1.398 Mg m3
Orthorhombic, Pna21Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2c -2nCell parameters from 17 reflections
a = 11.788 (2) Åθ = 38.5–39.8°
b = 6.6204 (16) ŵ = 1.76 mm1
c = 25.057 (3) ÅT = 293 K
V = 1955.5 (6) Å3Tabular, pink
Z = 40.50 × 0.40 × 0.15 mm
Data collection top
Rigaku AFC5R
diffractometer
1919 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anodeRint = 0.000
Graphite monochromatorθmax = 79.1°, θmin = 3.5°
ω–2θ scansh = 014
Absorption correction: ψ scans (north et al., 1968)k = 08
Tmin = 0.544, Tmax = 0.768l = 310
2102 measured reflections3 standard reflections every 150 reflections
2102 independent reflections intensity decay: 1.2%
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.07Calculated w = 1/[σ2(Fo2) + (0.065P)2 + 0.3269P]
where P = (Fo2 + 2Fc2)/3
2102 reflections(Δ/σ)max = 0.001
264 parametersΔρmax = 0.22 e Å3
1 restraintΔρmin = 0.20 e Å3
Special details top

Experimental. The scan width was (0.94 + 0.30tanθ)° with an ω scan speed of 8° per minute (up to 4 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

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
S10.21915 (7)0.11439 (13)0.40862 (3)0.0452 (2)
O10.2935 (2)0.2699 (4)0.38861 (12)0.0599 (7)
O20.1228 (2)0.1706 (5)0.43971 (11)0.0641 (8)
O30.2094 (2)0.4180 (4)0.25519 (11)0.0519 (6)
O40.3506 (4)0.0257 (7)0.11228 (16)0.0953 (13)
N10.1756 (3)0.0101 (6)0.35761 (11)0.0529 (8)
H10.21820.00780.32980.063*
N20.0576 (2)0.1086 (4)0.30046 (11)0.0387 (6)
H20.07210.19170.32590.046*
N30.2003 (2)0.2209 (5)0.17757 (12)0.0462 (7)
H30.21690.11400.19540.055*
C10.0696 (3)0.1280 (5)0.35373 (14)0.0424 (7)
H1A0.02280.10410.38540.051*
C20.0919 (4)0.3553 (6)0.34740 (18)0.0599 (11)
H2A0.02070.42780.35020.072*
H2B0.14090.40070.37610.072*
C30.1474 (4)0.4046 (6)0.29404 (16)0.0553 (9)
H3A0.21690.32730.29050.066*
H3B0.16720.54680.29320.066*
C40.0690 (3)0.3568 (5)0.24688 (16)0.0461 (8)
H40.00980.46070.24640.055*
C50.0102 (3)0.1553 (5)0.25561 (13)0.0394 (7)
C60.0069 (3)0.0602 (4)0.30458 (13)0.0376 (6)
C70.0532 (3)0.0384 (5)0.22032 (14)0.0422 (7)
H70.06460.06490.18430.051*
C80.0962 (3)0.1252 (5)0.24869 (13)0.0393 (7)
C90.1691 (3)0.2796 (5)0.22912 (13)0.0434 (7)
H90.18770.27480.19310.052*
C100.1285 (3)0.3660 (5)0.19395 (15)0.0461 (8)
C110.1241 (4)0.5107 (7)0.15453 (19)0.0665 (12)
H110.08060.62780.15510.080*
C120.1959 (4)0.4509 (8)0.11400 (19)0.0679 (12)
H120.20980.52180.08260.082*
C130.2435 (3)0.2687 (7)0.12794 (14)0.0532 (9)
C140.3179 (4)0.1401 (9)0.09877 (17)0.0672 (12)
H140.34390.18810.06610.081*
C150.3036 (3)0.0469 (5)0.44833 (13)0.0409 (7)
C160.4077 (3)0.0159 (6)0.46530 (15)0.0486 (8)
H160.43630.14040.45460.058*
C170.4704 (3)0.1085 (7)0.49879 (17)0.0578 (10)
H170.54090.06480.51080.069*
C180.4309 (3)0.2954 (6)0.51467 (14)0.0502 (8)
C190.3263 (5)0.3549 (7)0.49646 (19)0.0701 (13)
H190.29860.48170.50580.084*
C200.2614 (4)0.2302 (8)0.46457 (19)0.0705 (13)
H200.18920.27030.45410.085*
C210.4998 (5)0.4280 (8)0.5517 (2)0.0766 (14)
H21A0.55420.50330.53140.115*
H21B0.53860.34500.57730.115*
H21C0.45020.51970.57010.115*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0459 (4)0.0519 (4)0.0379 (3)0.0048 (3)0.0023 (4)0.0088 (4)
O10.0728 (18)0.0518 (15)0.0550 (14)0.0041 (12)0.0077 (13)0.0121 (12)
O20.0577 (16)0.0798 (19)0.0547 (16)0.0191 (15)0.0007 (13)0.0010 (15)
O30.0545 (14)0.0518 (13)0.0496 (13)0.0133 (12)0.0049 (11)0.0079 (12)
O40.109 (3)0.105 (3)0.071 (2)0.024 (3)0.034 (2)0.012 (2)
N10.0464 (16)0.080 (2)0.0322 (13)0.0037 (16)0.0029 (12)0.0086 (14)
N20.0389 (13)0.0378 (12)0.0393 (13)0.0030 (10)0.0009 (11)0.0044 (11)
N30.0481 (15)0.0498 (16)0.0407 (13)0.0022 (13)0.0025 (12)0.0119 (12)
C10.0430 (18)0.0459 (17)0.0382 (15)0.0032 (14)0.0048 (13)0.0064 (14)
C20.073 (3)0.051 (2)0.056 (2)0.0121 (19)0.013 (2)0.0173 (18)
C30.064 (2)0.0423 (18)0.060 (2)0.0150 (16)0.0084 (19)0.0072 (17)
C40.0437 (18)0.0342 (15)0.060 (2)0.0010 (13)0.0059 (16)0.0079 (15)
C50.0309 (15)0.0405 (15)0.0468 (17)0.0032 (12)0.0026 (13)0.0049 (13)
C60.0339 (15)0.0365 (14)0.0425 (16)0.0006 (12)0.0023 (13)0.0002 (13)
C70.0369 (15)0.0488 (17)0.0409 (16)0.0040 (14)0.0003 (13)0.0080 (14)
C80.0352 (15)0.0427 (16)0.0398 (15)0.0036 (12)0.0001 (12)0.0010 (14)
C90.0408 (17)0.0488 (18)0.0406 (16)0.0026 (14)0.0010 (13)0.0059 (15)
C100.0412 (17)0.0424 (17)0.055 (2)0.0065 (14)0.0029 (15)0.0140 (15)
C110.064 (2)0.060 (2)0.075 (3)0.0014 (19)0.009 (2)0.030 (2)
C120.068 (3)0.080 (3)0.056 (2)0.012 (2)0.004 (2)0.032 (2)
C130.053 (2)0.066 (2)0.0406 (16)0.0153 (18)0.0020 (16)0.0137 (17)
C140.070 (3)0.089 (3)0.0426 (19)0.018 (2)0.0086 (19)0.004 (2)
C150.0411 (16)0.0477 (17)0.0340 (14)0.0016 (14)0.0025 (12)0.0062 (13)
C160.0474 (18)0.053 (2)0.0457 (17)0.0051 (15)0.0062 (15)0.0001 (16)
C170.0421 (19)0.074 (2)0.057 (2)0.0001 (17)0.0123 (17)0.002 (2)
C180.055 (2)0.058 (2)0.0381 (16)0.0137 (17)0.0061 (15)0.0017 (15)
C190.091 (3)0.059 (2)0.060 (2)0.017 (2)0.023 (2)0.022 (2)
C200.064 (2)0.079 (3)0.069 (3)0.025 (2)0.028 (2)0.033 (2)
C210.089 (3)0.080 (3)0.061 (3)0.026 (3)0.020 (2)0.008 (2)
Geometric parameters (Å, º) top
S1—O21.427 (3)C5—C71.392 (5)
S1—O11.443 (3)C7—C81.392 (5)
S1—N11.605 (3)C7—H70.9300
S1—C151.767 (3)C8—C91.422 (5)
O3—C91.222 (4)C9—H90.9300
O4—C141.212 (7)C10—C111.377 (5)
N1—C11.476 (5)C11—C121.380 (7)
N1—H10.8600C11—H110.9300
N2—C61.356 (4)C12—C131.376 (7)
N2—C81.379 (4)C12—H120.9300
N2—H20.8600C13—C141.423 (7)
N3—C101.344 (5)C14—H140.9300
N3—C131.381 (5)C15—C161.364 (5)
N3—H30.8600C15—C201.373 (6)
C1—C61.505 (5)C16—C171.389 (5)
C1—C21.536 (5)C16—H160.9300
C1—H1A0.9800C17—C181.381 (6)
C2—C31.524 (6)C17—H170.9300
C2—H2A0.9700C18—C191.372 (6)
C2—H2B0.9700C18—C211.514 (6)
C3—C41.533 (6)C19—C201.380 (6)
C3—H3A0.9700C19—H190.9300
C3—H3B0.9700C20—H200.9300
C4—C101.501 (5)C21—H21A0.9600
C4—C51.519 (4)C21—H21B0.9600
C4—H40.9800C21—H21C0.9600
C5—C61.380 (5)
O2—S1—O1119.18 (19)C5—C7—H7126.2
O2—S1—N1108.29 (18)N2—C8—C7107.3 (3)
O1—S1—N1106.52 (17)N2—C8—C9125.5 (3)
O2—S1—C15107.38 (16)C7—C8—C9127.1 (3)
O1—S1—C15106.56 (16)O3—C9—C8126.1 (3)
N1—S1—C15108.57 (18)O3—C9—H9116.9
C1—N1—S1126.5 (2)C8—C9—H9116.9
C1—N1—H1116.7N3—C10—C11107.5 (4)
S1—N1—H1116.7N3—C10—C4122.3 (3)
C6—N2—C8108.8 (3)C11—C10—C4130.1 (4)
C6—N2—H2125.6C10—C11—C12107.8 (4)
C8—N2—H2125.6C10—C11—H11126.1
C10—N3—C13110.1 (3)C12—C11—H11126.1
C10—N3—H3124.9C13—C12—C11108.3 (4)
C13—N3—H3124.9C13—C12—H12125.8
N1—C1—C6108.2 (3)C11—C12—H12125.8
N1—C1—C2112.3 (3)C12—C13—N3106.2 (4)
C6—C1—C2107.0 (3)C12—C13—C14130.2 (4)
N1—C1—H1A109.8N3—C13—C14123.6 (4)
C6—C1—H1A109.8O4—C14—C13126.4 (4)
C2—C1—H1A109.8O4—C14—H14116.8
C3—C2—C1112.0 (3)C13—C14—H14116.8
C3—C2—H2A109.2C16—C15—C20120.2 (3)
C1—C2—H2A109.2C16—C15—S1119.9 (3)
C3—C2—H2B109.2C20—C15—S1119.8 (3)
C1—C2—H2B109.2C15—C16—C17119.1 (4)
H2A—C2—H2B107.9C15—C16—H16120.4
C2—C3—C4111.9 (3)C17—C16—H16120.4
C2—C3—H3A109.2C18—C17—C16121.7 (4)
C4—C3—H3A109.2C18—C17—H17119.1
C2—C3—H3B109.2C16—C17—H17119.1
C4—C3—H3B109.2C19—C18—C17117.7 (3)
H3A—C3—H3B107.9C19—C18—C21121.3 (4)
C10—C4—C5112.1 (3)C17—C18—C21121.0 (4)
C10—C4—C3113.0 (3)C18—C19—C20121.2 (4)
C5—C4—C3110.2 (3)C18—C19—H19119.4
C10—C4—H4107.1C20—C19—H19119.4
C5—C4—H4107.1C15—C20—C19120.0 (4)
C3—C4—H4107.1C15—C20—H20120.0
C6—C5—C7107.2 (3)C19—C20—H20120.0
C6—C5—C4122.8 (3)C18—C21—H21A109.5
C7—C5—C4129.9 (3)C18—C21—H21B109.5
N2—C6—C5108.9 (3)H21A—C21—H21B109.5
N2—C6—C1125.7 (3)C18—C21—H21C109.5
C5—C6—C1125.3 (3)H21A—C21—H21C109.5
C8—C7—C5107.7 (3)H21B—C21—H21C109.5
C8—C7—H7126.2
O2—S1—N1—C125.9 (4)C13—N3—C10—C110.2 (4)
O1—S1—N1—C1155.3 (3)C13—N3—C10—C4179.4 (3)
C15—S1—N1—C190.3 (3)C5—C4—C10—N350.6 (5)
S1—N1—C1—C6128.0 (3)C3—C4—C10—N374.7 (4)
S1—N1—C1—C2114.1 (4)C5—C4—C10—C11129.9 (4)
N1—C1—C2—C367.1 (5)C3—C4—C10—C11104.8 (5)
C6—C1—C2—C351.5 (5)N3—C10—C11—C120.6 (5)
C1—C2—C3—C464.8 (5)C4—C10—C11—C12178.9 (4)
C2—C3—C4—C10169.0 (3)C10—C11—C12—C130.7 (5)
C2—C3—C4—C542.7 (4)C11—C12—C13—N30.6 (5)
C10—C4—C5—C6142.0 (3)C11—C12—C13—C14176.3 (4)
C3—C4—C5—C615.2 (4)C10—N3—C13—C120.3 (4)
C10—C4—C5—C741.9 (5)C10—N3—C13—C14176.9 (4)
C3—C4—C5—C7168.7 (3)C12—C13—C14—O4174.7 (5)
C8—N2—C6—C50.4 (3)N3—C13—C14—O41.8 (8)
C8—N2—C6—C1176.9 (3)O2—S1—C15—C16112.6 (3)
C7—C5—C6—N20.9 (4)O1—S1—C15—C1616.2 (3)
C4—C5—C6—N2176.0 (3)N1—S1—C15—C16130.5 (3)
C7—C5—C6—C1176.3 (3)O2—S1—C15—C2063.6 (4)
C4—C5—C6—C16.8 (5)O1—S1—C15—C20167.6 (4)
N1—C1—C6—N279.7 (4)N1—S1—C15—C2053.3 (4)
C2—C1—C6—N2159.1 (3)C20—C15—C16—C170.5 (6)
N1—C1—C6—C597.1 (4)S1—C15—C16—C17176.6 (3)
C2—C1—C6—C524.1 (5)C15—C16—C17—C181.0 (6)
C6—C5—C7—C81.1 (4)C16—C17—C18—C190.4 (6)
C4—C5—C7—C8175.5 (3)C16—C17—C18—C21179.2 (4)
C6—N2—C8—C70.3 (3)C17—C18—C19—C201.8 (7)
C6—N2—C8—C9178.2 (3)C21—C18—C19—C20177.1 (5)
C5—C7—C8—N20.9 (4)C16—C15—C20—C192.6 (7)
C5—C7—C8—C9177.5 (3)S1—C15—C20—C19178.7 (4)
N2—C8—C9—O31.2 (6)C18—C19—C20—C153.3 (8)
C7—C8—C9—O3177.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.862.142.966 (4)161
N2—H2···O1ii0.862.252.934 (4)137
N3—H3···O3i0.862.162.989 (4)161
Symmetry codes: (i) x+1/2, y1/2, z; (ii) x1/2, y1/2, z.
 

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