The title compound, C17H13NOSe, has the expected planar indole core and is a rare case of a heavy-atom structure with positional disorder affecting only the heavy atom; the Se atom is disordered over two positions, with equal site-occupation factors (from refinement).
Supporting information
CCDC reference: 255878
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.007 Å
- R factor = 0.045
- wR factor = 0.108
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT241_ALERT_2_B Check High U(eq) as Compared to Neighbors for Se2
Alert level C
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C1
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C13
PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C13 - C14 ... 1.37 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C13 - C18 ... 1.36 Ang.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1998); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXTL-Plus.
Se-Phenyl 3-(1
H-indol-3-yl)selenoacrylate
top
Crystal data top
C17H13NOSe | Dx = 1.461 Mg m−3 |
Mr = 326.24 | Melting point: 437 K |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 69 reflections |
a = 15.7845 (16) Å | θ = 4.6–12.5° |
b = 10.0900 (13) Å | µ = 2.53 mm−1 |
c = 18.629 (3) Å | T = 296 K |
V = 2967.0 (7) Å3 | Plate, yellow |
Z = 8 | 0.60 × 0.28 × 0.16 mm |
F(000) = 1312 | |
Data collection top
Bruker P4 diffractometer | 1314 reflections with I > 2σ(I)' |
Radiation source: fine-focus sealed tube, FN4 | Rint = 0.052 |
Graphite monochromator | θmax = 25.0°, θmin = 2.2° |
ω scans | h = −18→1 |
Absorption correction: ψ scan (XSCANS; Siemens, 1996) | k = −11→9 |
Tmin = 0.428, Tmax = 0.667 | l = −22→1 |
5420 measured reflections | 3 standard reflections every 97 reflections |
2603 independent reflections | intensity decay: 1% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.108 | w = 1/[σ2(Fo2) + (0.0405P)2 + 0.2818P] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max = 0.001 |
2603 reflections | Δρmax = 0.21 e Å−3 |
191 parameters | Δρmin = −0.30 e Å−3 |
0 restraints | Extinction correction: SHELXTL-Plus, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0011 (2) |
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 | Occ. (<1) |
Se1 | 0.2752 (4) | 0.0353 (6) | 0.2835 (2) | 0.0810 (9) | 0.50 |
Se2 | 0.2755 (4) | −0.0020 (6) | 0.3017 (3) | 0.1068 (15) | 0.50 |
C1 | 0.3234 (2) | 0.1129 (4) | 0.3712 (2) | 0.0612 (10) | |
O1 | 0.28119 (17) | 0.1858 (3) | 0.40701 (16) | 0.0896 (9) | |
C2 | 0.4131 (2) | 0.0869 (4) | 0.3817 (2) | 0.0611 (10) | |
H2A | 0.4410 | 0.0283 | 0.3513 | 0.073* | |
C3 | 0.4558 (3) | 0.1459 (4) | 0.4344 (2) | 0.0630 (11) | |
H3A | 0.4245 | 0.2035 | 0.4629 | 0.076* | |
C4 | 0.5434 (3) | 0.1329 (4) | 0.4531 (2) | 0.0635 (11) | |
C5 | 0.5805 (3) | 0.2085 (4) | 0.5056 (2) | 0.0829 (13) | |
H5A | 0.5526 | 0.2722 | 0.5329 | 0.099* | |
N6 | 0.6635 (3) | 0.1771 (4) | 0.5122 (2) | 0.0900 (12) | |
H6A | 0.6984 | 0.2129 | 0.5419 | 0.108* | |
C7 | 0.7603 (3) | 0.0150 (6) | 0.4520 (3) | 0.0993 (17) | |
H7A | 0.8089 | 0.0387 | 0.4771 | 0.119* | |
C8 | 0.7617 (3) | −0.0836 (6) | 0.4024 (3) | 0.0975 (16) | |
H8A | 0.8122 | −0.1278 | 0.3932 | 0.117* | |
C9 | 0.6886 (3) | −0.1201 (5) | 0.3648 (3) | 0.0864 (14) | |
H9A | 0.6912 | −0.1891 | 0.3318 | 0.104* | |
C10 | 0.6127 (3) | −0.0555 (4) | 0.3758 (2) | 0.0710 (12) | |
H10A | 0.5646 | −0.0800 | 0.3502 | 0.085* | |
C11 | 0.6089 (3) | 0.0474 (4) | 0.4260 (2) | 0.0611 (11) | |
C12 | 0.6832 (3) | 0.0797 (5) | 0.4641 (3) | 0.0729 (12) | |
C13 | 0.1592 (3) | 0.0597 (4) | 0.3053 (2) | 0.0706 (12) | |
C14 | 0.1233 (3) | 0.1661 (5) | 0.2717 (3) | 0.0929 (15) | |
H14A | 0.1564 | 0.2224 | 0.2439 | 0.111* | |
C15 | 0.0364 (4) | 0.1900 (6) | 0.2794 (3) | 0.1043 (17) | |
H15A | 0.0115 | 0.2627 | 0.2572 | 0.125* | |
C16 | −0.0113 (3) | 0.1057 (7) | 0.3198 (3) | 0.1049 (18) | |
H16A | −0.0691 | 0.1204 | 0.3247 | 0.126* | |
C17 | 0.0247 (3) | 0.0022 (5) | 0.3523 (3) | 0.1109 (19) | |
H17A | −0.0083 | −0.0542 | 0.3802 | 0.133* | |
C18 | 0.1099 (4) | −0.0222 (4) | 0.3450 (3) | 0.0945 (15) | |
H18A | 0.1339 | −0.0954 | 0.3675 | 0.113* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Se1 | 0.0539 (11) | 0.119 (3) | 0.0705 (12) | 0.0130 (14) | −0.0004 (10) | −0.0277 (11) |
Se2 | 0.0644 (13) | 0.125 (3) | 0.131 (4) | 0.0287 (17) | −0.029 (2) | −0.063 (2) |
C1 | 0.052 (2) | 0.068 (3) | 0.064 (3) | 0.001 (2) | 0.009 (2) | 0.002 (2) |
O1 | 0.0672 (18) | 0.112 (2) | 0.090 (2) | 0.0257 (18) | 0.0040 (18) | −0.0280 (19) |
C2 | 0.052 (2) | 0.071 (3) | 0.060 (3) | 0.001 (2) | 0.008 (2) | −0.005 (2) |
C3 | 0.072 (3) | 0.062 (3) | 0.055 (3) | −0.003 (2) | 0.004 (2) | −0.003 (2) |
C4 | 0.066 (3) | 0.062 (3) | 0.063 (3) | −0.017 (2) | −0.011 (2) | 0.007 (2) |
C5 | 0.091 (3) | 0.079 (3) | 0.079 (3) | −0.021 (3) | −0.011 (3) | 0.004 (3) |
N6 | 0.091 (3) | 0.093 (3) | 0.086 (3) | −0.035 (2) | −0.028 (3) | 0.007 (2) |
C7 | 0.066 (4) | 0.138 (5) | 0.094 (4) | −0.025 (4) | −0.020 (3) | 0.039 (4) |
C8 | 0.062 (3) | 0.128 (5) | 0.102 (4) | 0.002 (3) | 0.004 (3) | 0.043 (4) |
C9 | 0.065 (3) | 0.103 (4) | 0.092 (4) | 0.005 (3) | 0.009 (3) | 0.018 (3) |
C10 | 0.056 (3) | 0.080 (3) | 0.077 (3) | −0.007 (2) | −0.004 (2) | 0.004 (2) |
C11 | 0.057 (3) | 0.059 (3) | 0.068 (3) | −0.017 (2) | −0.012 (2) | 0.011 (2) |
C12 | 0.064 (3) | 0.078 (3) | 0.077 (3) | −0.023 (3) | −0.012 (3) | 0.020 (3) |
C13 | 0.056 (2) | 0.076 (3) | 0.079 (3) | 0.004 (2) | −0.006 (2) | −0.016 (2) |
C14 | 0.102 (4) | 0.080 (3) | 0.097 (4) | 0.002 (3) | 0.005 (3) | −0.006 (3) |
C15 | 0.110 (4) | 0.099 (4) | 0.104 (4) | 0.045 (4) | −0.029 (4) | −0.013 (3) |
C16 | 0.063 (3) | 0.124 (5) | 0.128 (5) | 0.014 (3) | −0.021 (3) | −0.042 (4) |
C17 | 0.076 (4) | 0.095 (4) | 0.161 (6) | −0.009 (3) | 0.008 (4) | −0.006 (4) |
C18 | 0.091 (4) | 0.075 (3) | 0.118 (4) | 0.012 (3) | −0.010 (4) | 0.003 (3) |
Geometric parameters (Å, º) top
Se1—C1 | 1.965 (7) | C8—C9 | 1.398 (6) |
Se1—C13 | 1.892 (7) | C8—H8A | 0.9300 |
Se2—C1 | 1.894 (8) | C9—C10 | 1.379 (5) |
Se2—C13 | 1.940 (8) | C9—H9A | 0.9300 |
C1—O1 | 1.196 (4) | C10—C11 | 1.399 (5) |
C1—C2 | 1.454 (5) | C10—H10A | 0.9300 |
C2—C3 | 1.331 (5) | C11—C12 | 1.408 (5) |
C2—H2A | 0.9300 | C13—C18 | 1.355 (6) |
C3—C4 | 1.433 (5) | C13—C14 | 1.366 (6) |
C3—H3A | 0.9300 | C14—C15 | 1.400 (6) |
C4—C5 | 1.372 (5) | C14—H14A | 0.9300 |
C4—C11 | 1.437 (5) | C15—C16 | 1.362 (6) |
C5—N6 | 1.353 (5) | C15—H15A | 0.9300 |
C5—H5A | 0.9300 | C16—C17 | 1.334 (6) |
N6—C12 | 1.366 (5) | C16—H16A | 0.9300 |
N6—H6A | 0.8600 | C17—C18 | 1.374 (7) |
C7—C8 | 1.359 (6) | C17—H17A | 0.9300 |
C7—C12 | 1.400 (6) | C18—H18A | 0.9300 |
C7—H7A | 0.9300 | | |
| | | |
C1—Se1—C13 | 98.2 (3) | C8—C9—H9A | 119.4 |
C1—Se2—C13 | 99.0 (3) | C9—C10—C11 | 119.2 (4) |
O1—C1—C2 | 125.3 (4) | C9—C10—H10A | 120.4 |
O1—C1—Se1 | 119.6 (3) | C11—C10—H10A | 120.4 |
O1—C1—Se2 | 122.4 (4) | C10—C11—C12 | 118.2 (4) |
C2—C1—Se1 | 114.6 (3) | C10—C11—C4 | 135.3 (4) |
C2—C1—Se2 | 111.7 (3) | C12—C11—C4 | 106.4 (4) |
C1—C2—C3 | 120.8 (4) | N6—C12—C7 | 129.7 (5) |
C3—C2—H2A | 119.6 | N6—C12—C11 | 107.9 (4) |
C1—C2—H2A | 119.6 | C7—C12—C11 | 122.4 (5) |
C2—C3—C4 | 128.9 (4) | C18—C13—C14 | 119.4 (4) |
C2—C3—H3A | 115.6 | C18—C13—Se1 | 126.5 (4) |
C4—C3—H3A | 115.6 | C14—C13—Se1 | 114.0 (4) |
C5—C4—C3 | 122.4 (4) | C18—C13—Se2 | 111.5 (4) |
C5—C4—C11 | 106.1 (4) | C14—C13—Se2 | 129.1 (4) |
C3—C4—C11 | 131.6 (4) | C13—C14—C15 | 119.7 (5) |
N6—C5—C4 | 110.3 (4) | C13—C14—H14A | 120.1 |
N6—C5—H5A | 124.8 | C15—C14—H14A | 120.1 |
C4—C5—H5A | 124.8 | C16—C15—C14 | 119.4 (5) |
C5—N6—C12 | 109.2 (4) | C16—C15—H15A | 120.3 |
C5—N6—H6A | 125.4 | C14—C15—H15A | 120.3 |
C12—N6—H6A | 125.4 | C17—C16—C15 | 120.3 (5) |
C8—C7—C12 | 117.7 (5) | C17—C16—H16A | 119.9 |
C8—C7—H7A | 121.2 | C15—C16—H16A | 119.9 |
C12—C7—H7A | 121.2 | C16—C17—C18 | 120.8 (5) |
C7—C8—C9 | 121.4 (5) | C16—C17—H17A | 119.6 |
C7—C8—H8A | 119.3 | C18—C17—H17A | 119.6 |
C9—C8—H8A | 119.3 | C13—C18—C17 | 120.5 (5) |
C10—C9—C8 | 121.2 (5) | C13—C18—H18A | 119.8 |
C10—C9—H9A | 119.4 | C17—C18—H18A | 119.8 |
| | | |
C13—Se1—C1—O1 | −19.7 (4) | C8—C7—C12—N6 | 177.1 (4) |
Se2—Se1—C1—C2 | 82.0 (13) | C8—C7—C12—C11 | −1.1 (7) |
C13—Se1—C1—C2 | 167.3 (3) | C10—C11—C12—N6 | −176.9 (3) |
Se1—Se2—C1—O1 | 83.8 (14) | C4—C11—C12—N6 | 1.0 (4) |
C13—Se2—C1—O1 | 6.8 (4) | C10—C11—C12—C7 | 1.7 (6) |
Se1—Se2—C1—C2 | −104.4 (13) | C4—C11—C12—C7 | 179.6 (4) |
C13—Se2—C1—C2 | 178.7 (3) | Se2—Se1—C13—C18 | −10.6 (17) |
O1—C1—C2—C3 | −0.2 (6) | C1—Se1—C13—C18 | −84.7 (5) |
Se1—C1—C2—C3 | 172.3 (3) | Se2—Se1—C13—C14 | 174.9 (14) |
Se2—C1—C2—C3 | −171.7 (3) | C1—Se1—C13—C14 | 100.9 (4) |
C1—C2—C3—C4 | 179.9 (4) | C1—Se1—C13—Se2 | −74.1 (14) |
C2—C3—C4—C5 | 174.7 (4) | Se1—Se2—C13—C18 | 170.8 (14) |
C2—C3—C4—C11 | −5.7 (7) | C1—Se2—C13—C18 | −100.8 (4) |
C3—C4—C5—N6 | −179.6 (3) | Se1—Se2—C13—C14 | −6.0 (17) |
C11—C4—C5—N6 | 0.7 (5) | C1—Se2—C13—C14 | 82.4 (5) |
C4—C5—N6—C12 | −0.1 (5) | C1—Se2—C13—Se1 | 88.4 (15) |
C12—C7—C8—C9 | −0.3 (7) | C18—C13—C14—C15 | 0.8 (7) |
C7—C8—C9—C10 | 1.2 (7) | Se1—C13—C14—C15 | 175.6 (4) |
C8—C9—C10—C11 | −0.6 (7) | Se2—C13—C14—C15 | 177.4 (4) |
C9—C10—C11—C12 | −0.8 (6) | C13—C14—C15—C16 | −0.7 (8) |
C9—C10—C11—C4 | −177.9 (4) | C14—C15—C16—C17 | 0.7 (8) |
C5—C4—C11—C10 | 176.3 (4) | C15—C16—C17—C18 | −0.7 (9) |
C3—C4—C11—C10 | −3.3 (8) | C14—C13—C18—C17 | −0.8 (7) |
C5—C4—C11—C12 | −1.1 (4) | Se1—C13—C18—C17 | −175.0 (5) |
C3—C4—C11—C12 | 179.3 (4) | Se2—C13—C18—C17 | −178.0 (5) |
C5—N6—C12—C7 | −179.0 (4) | C16—C17—C18—C13 | 0.8 (8) |
C5—N6—C12—C11 | −0.6 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N6—H6A···O1i | 0.86 | 1.91 | 2.762 (5) | 169 |
Symmetry code: (i) x+1/2, −y+1/2, −z+1. |