In the title compound, C
21H
15NO
3S
2, the phenyl ring of the phenylsulfonyl substituent makes a dihedral angle of 73.6 (1)° with the mean plane of the indole ring system, whereas the phenyl ring of the phenylsulfanyl group forms a dihedral angle of 73.9 (1)° with the mean plane of the indole ring system. The crystal packing is stabilized by C—H
O interactions.
Supporting information
CCDC reference: 604971
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.037
- wR factor = 0.113
- Data-to-parameter ratio = 13.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - O2 .. 6.30 su
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C9 -C14 1.37 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 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
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: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 2000); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
3-Phenylsulfanyl-1-phenylsulfonyl-1
H-indole-2-carbaldehyde
top
Crystal data top
C21H15NO3S2 | F(000) = 816 |
Mr = 393.46 | Dx = 1.403 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 10.003 (4) Å | θ = 4.4–18.0° |
b = 16.001 (6) Å | µ = 0.31 mm−1 |
c = 11.750 (5) Å | T = 293 K |
β = 97.80 (3)° | Block, colourless |
V = 1863.3 (13) Å3 | 0.32 × 0.23 × 0.18 mm |
Z = 4 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.021 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.1° |
Graphite monochromator | h = 0→11 |
Non–profiled w/2θ scans | k = −1→19 |
3729 measured reflections | l = −13→13 |
3267 independent reflections | 3 standard reflections every 100 reflections |
2080 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0627P)2] where P = (Fo2 + 2Fc2)/3 |
3267 reflections | (Δ/σ)max < 0.001 |
244 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Special details top
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 | x | y | z | Uiso*/Ueq | |
S1 | 0.70581 (7) | 0.16886 (4) | 0.71889 (6) | 0.0599 (2) | |
S2 | 0.92190 (7) | −0.12779 (4) | 0.66480 (7) | 0.0626 (2) | |
N1 | 0.7031 (2) | 0.07888 (12) | 0.64334 (17) | 0.0494 (5) | |
O1 | 0.5753 (2) | 0.20439 (12) | 0.69220 (19) | 0.0800 (6) | |
O2 | 0.8231 (2) | 0.21249 (11) | 0.69469 (18) | 0.0785 (6) | |
O3 | 1.05919 (19) | 0.03597 (13) | 0.64970 (19) | 0.0788 (6) | |
C1 | 0.8248 (2) | 0.03186 (15) | 0.6474 (2) | 0.0480 (6) | |
C2 | 0.7954 (2) | −0.05149 (15) | 0.6532 (2) | 0.0465 (6) | |
C3 | 0.6510 (2) | −0.06034 (14) | 0.65174 (18) | 0.0426 (6) | |
C4 | 0.5635 (3) | −0.12869 (16) | 0.6510 (2) | 0.0492 (6) | |
H4 | 0.5966 | −0.1830 | 0.6529 | 0.059* | |
C5 | 0.4281 (3) | −0.11390 (18) | 0.6474 (2) | 0.0589 (7) | |
H5 | 0.3689 | −0.1588 | 0.6470 | 0.071* | |
C6 | 0.3780 (3) | −0.03306 (19) | 0.6443 (2) | 0.0584 (7) | |
H6 | 0.2856 | −0.0250 | 0.6418 | 0.070* | |
C7 | 0.4604 (3) | 0.03544 (17) | 0.6447 (2) | 0.0543 (7) | |
H7 | 0.4258 | 0.0895 | 0.6429 | 0.065* | |
C8 | 0.5976 (2) | 0.02078 (15) | 0.64812 (19) | 0.0437 (6) | |
C9 | 0.7299 (3) | 0.13755 (14) | 0.8633 (2) | 0.0514 (6) | |
C10 | 0.8591 (3) | 0.1215 (2) | 0.9154 (3) | 0.0721 (8) | |
H10 | 0.9314 | 0.1257 | 0.8736 | 0.086* | |
C11 | 0.8810 (3) | 0.0992 (2) | 1.0294 (3) | 0.0805 (10) | |
H11 | 0.9682 | 0.0881 | 1.0645 | 0.097* | |
C12 | 0.7753 (3) | 0.09320 (19) | 1.0913 (3) | 0.0705 (8) | |
H12 | 0.7903 | 0.0788 | 1.1686 | 0.085* | |
C13 | 0.6480 (3) | 0.1085 (2) | 1.0391 (3) | 0.0829 (10) | |
H13 | 0.5759 | 0.1035 | 1.0809 | 0.099* | |
C14 | 0.6240 (3) | 0.1313 (2) | 0.9250 (3) | 0.0717 (8) | |
H14 | 0.5366 | 0.1424 | 0.8903 | 0.086* | |
C15 | 0.9507 (3) | 0.06918 (19) | 0.6230 (2) | 0.0631 (7) | |
H15 | 0.9476 | 0.1205 | 0.5855 | 0.076* | |
C16 | 0.8391 (2) | −0.21720 (15) | 0.6000 (2) | 0.0485 (6) | |
C17 | 0.8354 (3) | −0.28956 (17) | 0.6640 (2) | 0.0602 (7) | |
H17 | 0.8707 | −0.2895 | 0.7414 | 0.072* | |
C18 | 0.7799 (3) | −0.36152 (19) | 0.6140 (3) | 0.0723 (9) | |
H18 | 0.7792 | −0.4102 | 0.6571 | 0.087* | |
C19 | 0.7257 (3) | −0.3613 (2) | 0.5006 (3) | 0.0744 (9) | |
H19 | 0.6881 | −0.4098 | 0.4666 | 0.089* | |
C20 | 0.7269 (3) | −0.2892 (2) | 0.4370 (3) | 0.0706 (8) | |
H20 | 0.6879 | −0.2890 | 0.3605 | 0.085* | |
C21 | 0.7852 (3) | −0.21717 (17) | 0.4854 (2) | 0.0580 (7) | |
H21 | 0.7883 | −0.1691 | 0.4414 | 0.070* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0747 (5) | 0.0408 (4) | 0.0640 (5) | 0.0109 (3) | 0.0088 (3) | 0.0007 (3) |
S2 | 0.0481 (4) | 0.0620 (4) | 0.0724 (5) | 0.0193 (3) | −0.0109 (3) | −0.0166 (4) |
N1 | 0.0521 (12) | 0.0478 (11) | 0.0482 (12) | 0.0078 (10) | 0.0070 (9) | −0.0014 (10) |
O1 | 0.0885 (14) | 0.0593 (12) | 0.0881 (14) | 0.0335 (11) | −0.0026 (11) | −0.0019 (11) |
O2 | 0.1002 (16) | 0.0477 (11) | 0.0911 (15) | −0.0143 (10) | 0.0249 (12) | 0.0095 (10) |
O3 | 0.0471 (11) | 0.0905 (15) | 0.0971 (16) | −0.0003 (11) | 0.0045 (10) | −0.0167 (13) |
C1 | 0.0439 (14) | 0.0536 (15) | 0.0460 (14) | 0.0091 (11) | 0.0041 (11) | −0.0047 (12) |
C2 | 0.0455 (13) | 0.0533 (15) | 0.0396 (13) | 0.0118 (11) | 0.0018 (10) | −0.0025 (11) |
C3 | 0.0441 (13) | 0.0490 (14) | 0.0343 (13) | 0.0093 (11) | 0.0041 (10) | 0.0023 (11) |
C4 | 0.0502 (14) | 0.0512 (14) | 0.0463 (14) | 0.0082 (12) | 0.0067 (11) | 0.0082 (12) |
C5 | 0.0523 (16) | 0.0700 (18) | 0.0554 (16) | −0.0005 (14) | 0.0104 (12) | 0.0131 (14) |
C6 | 0.0441 (14) | 0.083 (2) | 0.0499 (16) | 0.0124 (14) | 0.0127 (12) | 0.0096 (14) |
C7 | 0.0528 (15) | 0.0622 (16) | 0.0486 (15) | 0.0198 (13) | 0.0096 (12) | 0.0031 (12) |
C8 | 0.0462 (14) | 0.0507 (13) | 0.0345 (12) | 0.0116 (11) | 0.0062 (10) | 0.0015 (11) |
C9 | 0.0569 (16) | 0.0426 (13) | 0.0558 (16) | 0.0003 (12) | 0.0113 (13) | −0.0111 (12) |
C10 | 0.0543 (17) | 0.098 (2) | 0.064 (2) | −0.0081 (16) | 0.0111 (14) | −0.0004 (17) |
C11 | 0.0597 (19) | 0.112 (3) | 0.068 (2) | −0.0033 (18) | −0.0011 (16) | −0.0034 (19) |
C12 | 0.081 (2) | 0.076 (2) | 0.0543 (18) | −0.0068 (17) | 0.0100 (16) | −0.0086 (15) |
C13 | 0.068 (2) | 0.116 (3) | 0.069 (2) | −0.0035 (19) | 0.0262 (17) | −0.011 (2) |
C14 | 0.0551 (17) | 0.089 (2) | 0.072 (2) | 0.0122 (16) | 0.0130 (15) | −0.0087 (18) |
C15 | 0.0602 (18) | 0.0635 (17) | 0.0669 (18) | −0.0034 (15) | 0.0130 (14) | −0.0122 (14) |
C16 | 0.0438 (14) | 0.0517 (15) | 0.0498 (15) | 0.0155 (11) | 0.0056 (11) | −0.0022 (12) |
C17 | 0.0626 (17) | 0.0655 (18) | 0.0522 (16) | 0.0231 (14) | 0.0065 (13) | 0.0048 (14) |
C18 | 0.0643 (19) | 0.0574 (18) | 0.096 (3) | 0.0081 (15) | 0.0151 (17) | 0.0120 (17) |
C19 | 0.0583 (18) | 0.0653 (19) | 0.099 (3) | −0.0045 (15) | 0.0082 (17) | −0.0150 (19) |
C20 | 0.0636 (18) | 0.084 (2) | 0.0623 (18) | −0.0008 (16) | 0.0000 (14) | −0.0135 (18) |
C21 | 0.0618 (17) | 0.0588 (16) | 0.0521 (16) | 0.0056 (13) | 0.0028 (13) | 0.0033 (13) |
Geometric parameters (Å, º) top
S1—O1 | 1.419 (2) | C9—C10 | 1.377 (4) |
S1—O2 | 1.426 (2) | C10—C11 | 1.375 (4) |
S1—N1 | 1.690 (2) | C10—H10 | 0.9300 |
S1—C9 | 1.754 (3) | C11—C12 | 1.366 (4) |
S2—C2 | 1.750 (2) | C11—H11 | 0.9300 |
S2—C16 | 1.773 (3) | C12—C13 | 1.358 (4) |
N1—C8 | 1.414 (3) | C12—H12 | 0.9300 |
N1—C1 | 1.426 (3) | C13—C14 | 1.379 (4) |
O3—C15 | 1.211 (3) | C13—H13 | 0.9300 |
C1—C2 | 1.369 (3) | C14—H14 | 0.9300 |
C1—C15 | 1.457 (4) | C15—H15 | 0.9300 |
C2—C3 | 1.450 (3) | C16—C17 | 1.384 (3) |
C3—C4 | 1.400 (3) | C16—C21 | 1.380 (4) |
C3—C8 | 1.402 (3) | C17—C18 | 1.375 (4) |
C4—C5 | 1.370 (4) | C17—H17 | 0.9300 |
C4—H4 | 0.9300 | C18—C19 | 1.368 (4) |
C5—C6 | 1.386 (4) | C18—H18 | 0.9300 |
C5—H5 | 0.9300 | C19—C20 | 1.375 (4) |
C6—C7 | 1.371 (4) | C19—H19 | 0.9300 |
C6—H6 | 0.9300 | C20—C21 | 1.380 (4) |
C7—C8 | 1.387 (3) | C20—H20 | 0.9300 |
C7—H7 | 0.9300 | C21—H21 | 0.9300 |
C9—C14 | 1.366 (4) | | |
| | | |
O1—S1—O2 | 121.09 (13) | C9—C10—C11 | 119.8 (3) |
O1—S1—N1 | 106.05 (12) | C9—C10—H10 | 120.1 |
O2—S1—N1 | 105.50 (11) | C11—C10—H10 | 120.1 |
O1—S1—C9 | 109.27 (13) | C12—C11—C10 | 120.3 (3) |
O2—S1—C9 | 108.88 (13) | C12—C11—H11 | 119.8 |
N1—S1—C9 | 104.78 (11) | C10—C11—H11 | 119.8 |
C2—S2—C16 | 103.81 (12) | C13—C12—C11 | 119.5 (3) |
C8—N1—C1 | 106.87 (19) | C13—C12—H12 | 120.2 |
C8—N1—S1 | 119.89 (16) | C11—C12—H12 | 120.2 |
C1—N1—S1 | 118.63 (16) | C12—C13—C14 | 121.0 (3) |
C2—C1—N1 | 109.1 (2) | C12—C13—H13 | 119.5 |
C2—C1—C15 | 127.3 (2) | C14—C13—H13 | 119.5 |
N1—C1—C15 | 122.3 (2) | C9—C14—C13 | 119.4 (3) |
C1—C2—C3 | 108.3 (2) | C9—C14—H14 | 120.3 |
C1—C2—S2 | 121.73 (19) | C13—C14—H14 | 120.3 |
C3—C2—S2 | 129.91 (19) | O3—C15—C1 | 122.5 (3) |
C4—C3—C8 | 119.2 (2) | O3—C15—H15 | 118.7 |
C4—C3—C2 | 134.2 (2) | C1—C15—H15 | 118.7 |
C8—C3—C2 | 106.6 (2) | C17—C16—C21 | 119.7 (2) |
C5—C4—C3 | 118.7 (2) | C17—C16—S2 | 119.1 (2) |
C5—C4—H4 | 120.7 | C21—C16—S2 | 121.1 (2) |
C3—C4—H4 | 120.7 | C16—C17—C18 | 120.5 (3) |
C4—C5—C6 | 121.0 (3) | C16—C17—H17 | 119.8 |
C4—C5—H5 | 119.5 | C18—C17—H17 | 119.8 |
C6—C5—H5 | 119.5 | C17—C18—C19 | 119.8 (3) |
C7—C6—C5 | 122.1 (2) | C17—C18—H18 | 120.1 |
C7—C6—H6 | 119.0 | C19—C18—H18 | 120.1 |
C5—C6—H6 | 119.0 | C20—C19—C18 | 120.0 (3) |
C6—C7—C8 | 117.2 (2) | C20—C19—H19 | 120.0 |
C6—C7—H7 | 121.4 | C18—C19—H19 | 120.0 |
C8—C7—H7 | 121.4 | C21—C20—C19 | 120.7 (3) |
C3—C8—N1 | 109.05 (19) | C21—C20—H20 | 119.7 |
C3—C8—C7 | 121.9 (2) | C19—C20—H20 | 119.7 |
N1—C8—C7 | 129.0 (2) | C20—C21—C16 | 119.3 (3) |
C14—C9—C10 | 119.9 (3) | C20—C21—H21 | 120.3 |
C14—C9—S1 | 121.3 (2) | C16—C21—H21 | 120.3 |
C10—C9—S1 | 118.8 (2) | | |
| | | |
O1—S1—N1—C8 | −50.1 (2) | C1—N1—C8—C7 | −178.8 (2) |
O2—S1—N1—C8 | −179.65 (18) | S1—N1—C8—C7 | 42.5 (3) |
C9—S1—N1—C8 | 65.5 (2) | C6—C7—C8—C3 | −0.4 (4) |
O1—S1—N1—C1 | 175.90 (19) | C6—C7—C8—N1 | 176.3 (2) |
O2—S1—N1—C1 | 46.3 (2) | O1—S1—C9—C14 | 14.5 (3) |
C9—S1—N1—C1 | −68.6 (2) | O2—S1—C9—C14 | 148.7 (2) |
C8—N1—C1—C2 | 0.6 (3) | N1—S1—C9—C14 | −98.8 (2) |
S1—N1—C1—C2 | 139.99 (19) | O1—S1—C9—C10 | −163.6 (2) |
C8—N1—C1—C15 | 168.4 (2) | O2—S1—C9—C10 | −29.3 (2) |
S1—N1—C1—C15 | −52.3 (3) | N1—S1—C9—C10 | 83.2 (2) |
N1—C1—C2—C3 | 0.6 (3) | C14—C9—C10—C11 | 0.1 (4) |
C15—C1—C2—C3 | −166.4 (2) | S1—C9—C10—C11 | 178.1 (3) |
N1—C1—C2—S2 | −177.55 (16) | C9—C10—C11—C12 | −0.3 (5) |
C15—C1—C2—S2 | 15.5 (4) | C10—C11—C12—C13 | 0.8 (5) |
C16—S2—C2—C1 | −152.1 (2) | C11—C12—C13—C14 | −1.1 (5) |
C16—S2—C2—C3 | 30.2 (2) | C10—C9—C14—C13 | −0.4 (4) |
C1—C2—C3—C4 | 177.0 (2) | S1—C9—C14—C13 | −178.4 (2) |
S2—C2—C3—C4 | −5.1 (4) | C12—C13—C14—C9 | 0.9 (5) |
C1—C2—C3—C8 | −1.6 (3) | C2—C1—C15—O3 | −31.0 (4) |
S2—C2—C3—C8 | 176.36 (18) | N1—C1—C15—O3 | 163.6 (2) |
C8—C3—C4—C5 | −0.4 (3) | C2—S2—C16—C17 | −121.1 (2) |
C2—C3—C4—C5 | −178.8 (3) | C2—S2—C16—C21 | 62.7 (2) |
C3—C4—C5—C6 | 0.1 (4) | C21—C16—C17—C18 | 0.7 (4) |
C4—C5—C6—C7 | −0.1 (4) | S2—C16—C17—C18 | −175.6 (2) |
C5—C6—C7—C8 | 0.2 (4) | C16—C17—C18—C19 | −1.2 (4) |
C4—C3—C8—N1 | −176.8 (2) | C17—C18—C19—C20 | 0.0 (5) |
C2—C3—C8—N1 | 2.0 (2) | C18—C19—C20—C21 | 1.6 (5) |
C4—C3—C8—C7 | 0.5 (3) | C19—C20—C21—C16 | −2.0 (4) |
C2—C3—C8—C7 | 179.3 (2) | C17—C16—C21—C20 | 0.9 (4) |
C1—N1—C8—C3 | −1.6 (2) | S2—C16—C21—C20 | 177.1 (2) |
S1—N1—C8—C3 | −140.39 (17) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O3i | 0.93 | 2.48 | 3.387 (4) | 164 |
C7—H7···O1 | 0.93 | 2.39 | 2.961 (4) | 119 |
C15—H15···O2 | 0.93 | 2.41 | 2.807 (4) | 106 |
Symmetry code: (i) x−1, y, z. |