The title compound, C
20H
14N
2OS, was synthesized by mixing imidazolidine-2-thione, ethyl chloroacetate and anthracene-10-carbaldehyde in ethanol. The dihedral angle between the anthracene plane and the heterocyclic ring system is 61.5 (3)°. In the crystal structure, the molecules are linked
via weak C—H
O interactions.
Supporting information
CCDC reference: 263658
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.010 Å
- R factor = 0.074
- wR factor = 0.198
- Data-to-parameter ratio = 12.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 0.30
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C2
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 25.05
From the CIF: _reflns_number_total 2789
Count of symmetry unique reflns 1667
Completeness (_total/calc) 167.31%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1122
Fraction of Friedel pairs measured 0.673
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 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
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
(2
Z)-2-(anthracen-9-ylmethylene)-5,6-dihydroimidazo[2,1-
b]thiazol-3(2
H)-one
top
Crystal data top
C20H14N2OS | Dx = 1.383 Mg m−3 |
Mr = 330.39 | Melting point = 481–483 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1622 reflections |
a = 5.127 (2) Å | θ = 2.3–26.1° |
b = 13.750 (6) Å | µ = 0.21 mm−1 |
c = 22.503 (9) Å | T = 293 K |
V = 1586.4 (11) Å3 | Plate, colorless |
Z = 4 | 0.40 × 0.20 × 0.04 mm |
F(000) = 688 | |
Data collection top
Bruker SMART1000 CCD area detector diffractometer | 2789 independent reflections |
Radiation source: fine-focus sealed tube | 1531 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.089 |
φ and ω scans | θmax = 25.1°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −4→6 |
Tmin = 0.886, Tmax = 0.992 | k = −16→15 |
7748 measured reflections | l = −26→26 |
Refinement top
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0841P)2 + 0.2765P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.074 | (Δ/σ)max < 0.001 |
wR(F2) = 0.198 | Δρmax = 0.51 e Å−3 |
S = 1.12 | Δρmin = −0.54 e Å−3 |
2789 reflections | Absolute structure: Flack (1983), 883 Friedel pairs |
218 parameters | Absolute structure parameter: −0.2 (3) |
0 restraints | |
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 | 0.1235 (4) | −0.00074 (13) | −0.00642 (7) | 0.0551 (6) | |
O1 | 0.6529 (12) | −0.1756 (4) | 0.0522 (2) | 0.0684 (16) | |
N1 | 0.2434 (14) | −0.0751 (4) | −0.1159 (3) | 0.0610 (18) | |
N2 | 0.4756 (12) | −0.1259 (4) | −0.0366 (2) | 0.0454 (15) | |
C1 | 0.2790 (15) | −0.0699 (5) | −0.0609 (3) | 0.050 (2) | |
C2 | 0.434 (2) | −0.1478 (6) | −0.1374 (3) | 0.080 (3) | |
H2A | 0.5488 | −0.1188 | −0.1668 | 0.096* | |
H2B | 0.3445 | −0.2023 | −0.1555 | 0.096* | |
C3 | 0.5924 (17) | −0.1822 (5) | −0.0840 (3) | 0.059 (2) | |
H3A | 0.5714 | −0.2515 | −0.0773 | 0.071* | |
H3B | 0.7762 | −0.1673 | −0.0885 | 0.071* | |
C4 | 0.5033 (15) | −0.1245 (5) | 0.0231 (3) | 0.0443 (18) | |
C5 | 0.3221 (14) | −0.0500 (4) | 0.0492 (3) | 0.0408 (18) | |
C6 | 0.3145 (14) | −0.0286 (4) | 0.1060 (3) | 0.0441 (18) | |
H6 | 0.4280 | −0.0620 | 0.1309 | 0.053* | |
C7 | 0.1406 (14) | 0.0441 (4) | 0.1335 (3) | 0.0389 (16) | |
C8 | 0.1567 (13) | 0.1432 (4) | 0.1168 (2) | 0.0341 (15) | |
C9 | 0.3461 (15) | 0.1776 (4) | 0.0757 (3) | 0.0420 (17) | |
H9 | 0.4644 | 0.1345 | 0.0587 | 0.050* | |
C10 | 0.3540 (17) | 0.2743 (5) | 0.0611 (3) | 0.053 (2) | |
H10 | 0.4824 | 0.2964 | 0.0352 | 0.064* | |
C11 | 0.1727 (17) | 0.3409 (5) | 0.0843 (3) | 0.058 (2) | |
H11 | 0.1762 | 0.4057 | 0.0724 | 0.070* | |
C12 | −0.0089 (16) | 0.3096 (5) | 0.1244 (3) | 0.054 (2) | |
H12 | −0.1275 | 0.3538 | 0.1401 | 0.065* | |
C13 | −0.0200 (14) | 0.2098 (5) | 0.1427 (3) | 0.0417 (17) | |
C14 | −0.1988 (15) | 0.1810 (5) | 0.1846 (3) | 0.049 (2) | |
H14 | −0.3123 | 0.2266 | 0.2009 | 0.059* | |
C15 | −0.2121 (14) | 0.0842 (5) | 0.2031 (3) | 0.0425 (18) | |
C16 | −0.3895 (18) | 0.0525 (7) | 0.2470 (3) | 0.063 (2) | |
H16 | −0.5035 | 0.0973 | 0.2638 | 0.076* | |
C17 | −0.3986 (18) | −0.0417 (7) | 0.2655 (3) | 0.066 (2) | |
H17 | −0.5140 | −0.0605 | 0.2952 | 0.079* | |
C18 | −0.2336 (17) | −0.1094 (6) | 0.2394 (3) | 0.064 (2) | |
H18 | −0.2418 | −0.1741 | 0.2513 | 0.077* | |
C19 | −0.0597 (15) | −0.0826 (5) | 0.1966 (3) | 0.052 (2) | |
H19 | 0.0484 | −0.1294 | 0.1798 | 0.062* | |
C20 | −0.0403 (13) | 0.0151 (5) | 0.1774 (3) | 0.0392 (17) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0572 (13) | 0.0569 (10) | 0.0511 (10) | 0.0166 (10) | −0.0125 (10) | 0.0011 (10) |
O1 | 0.064 (4) | 0.075 (3) | 0.066 (3) | 0.027 (3) | −0.009 (3) | 0.009 (3) |
N1 | 0.077 (5) | 0.065 (4) | 0.041 (4) | −0.002 (4) | −0.005 (3) | −0.006 (3) |
N2 | 0.036 (4) | 0.054 (3) | 0.046 (3) | −0.003 (3) | 0.000 (3) | −0.002 (3) |
C1 | 0.049 (5) | 0.047 (4) | 0.054 (5) | −0.007 (4) | −0.007 (4) | 0.014 (4) |
C2 | 0.103 (8) | 0.092 (6) | 0.044 (5) | −0.001 (6) | 0.009 (5) | −0.004 (4) |
C3 | 0.051 (6) | 0.060 (5) | 0.067 (5) | −0.008 (4) | 0.021 (5) | −0.008 (4) |
C4 | 0.037 (5) | 0.052 (4) | 0.044 (4) | −0.004 (4) | −0.003 (4) | 0.005 (3) |
C5 | 0.034 (5) | 0.046 (4) | 0.042 (4) | −0.001 (3) | −0.002 (3) | 0.005 (3) |
C6 | 0.038 (5) | 0.045 (4) | 0.049 (4) | −0.001 (3) | −0.006 (4) | 0.006 (3) |
C7 | 0.034 (4) | 0.048 (4) | 0.035 (3) | −0.004 (3) | 0.002 (4) | −0.001 (3) |
C8 | 0.028 (4) | 0.044 (3) | 0.031 (3) | −0.005 (3) | −0.006 (3) | −0.006 (3) |
C9 | 0.041 (5) | 0.040 (4) | 0.045 (4) | 0.001 (3) | −0.007 (4) | −0.003 (3) |
C10 | 0.052 (6) | 0.056 (4) | 0.052 (4) | −0.012 (4) | 0.002 (4) | 0.006 (4) |
C11 | 0.057 (6) | 0.048 (4) | 0.068 (5) | 0.003 (4) | 0.003 (5) | −0.003 (4) |
C12 | 0.060 (6) | 0.042 (4) | 0.059 (4) | 0.014 (4) | 0.006 (4) | −0.011 (4) |
C13 | 0.041 (5) | 0.052 (4) | 0.032 (4) | 0.001 (4) | −0.003 (3) | −0.008 (3) |
C14 | 0.045 (5) | 0.052 (4) | 0.051 (4) | 0.004 (4) | 0.004 (4) | −0.010 (3) |
C15 | 0.028 (5) | 0.069 (5) | 0.030 (3) | −0.002 (4) | 0.004 (3) | −0.011 (3) |
C16 | 0.058 (6) | 0.084 (6) | 0.046 (5) | −0.014 (5) | −0.001 (5) | −0.014 (4) |
C17 | 0.055 (6) | 0.087 (6) | 0.056 (5) | −0.015 (5) | 0.009 (5) | 0.009 (5) |
C18 | 0.064 (6) | 0.073 (5) | 0.056 (5) | −0.018 (5) | −0.002 (5) | 0.019 (4) |
C19 | 0.051 (6) | 0.062 (5) | 0.043 (4) | 0.004 (4) | 0.000 (4) | 0.001 (4) |
C20 | 0.042 (5) | 0.041 (4) | 0.034 (3) | −0.011 (3) | −0.008 (3) | 0.000 (3) |
Geometric parameters (Å, º) top
S1—C1 | 1.744 (8) | C9—C10 | 1.371 (8) |
S1—C5 | 1.749 (6) | C9—H9 | 0.9300 |
O1—C4 | 1.229 (8) | C10—C11 | 1.405 (10) |
N1—C1 | 1.254 (8) | C10—H10 | 0.9300 |
N1—C2 | 1.481 (10) | C11—C12 | 1.367 (10) |
N2—C4 | 1.352 (8) | C11—H11 | 0.9300 |
N2—C1 | 1.381 (9) | C12—C13 | 1.434 (9) |
N2—C3 | 1.447 (8) | C12—H12 | 0.9300 |
C2—C3 | 1.524 (10) | C13—C14 | 1.373 (9) |
C2—H2A | 0.9700 | C14—C15 | 1.396 (9) |
C2—H2B | 0.9700 | C14—H14 | 0.9300 |
C3—H3A | 0.9700 | C15—C16 | 1.412 (10) |
C3—H3B | 0.9700 | C15—C20 | 1.418 (9) |
C4—C5 | 1.501 (9) | C16—C17 | 1.362 (10) |
C5—C6 | 1.312 (8) | C16—H16 | 0.9300 |
C6—C7 | 1.476 (8) | C17—C18 | 1.388 (11) |
C6—H6 | 0.9300 | C17—H17 | 0.9300 |
C7—C20 | 1.412 (9) | C18—C19 | 1.363 (10) |
C7—C8 | 1.416 (8) | C18—H18 | 0.9300 |
C8—C13 | 1.414 (8) | C19—C20 | 1.415 (9) |
C8—C9 | 1.423 (9) | C19—H19 | 0.9300 |
| | | |
C1—S1—C5 | 91.5 (3) | C10—C9—H9 | 120.0 |
C1—N1—C2 | 105.3 (7) | C8—C9—H9 | 120.0 |
C4—N2—C1 | 117.5 (6) | C9—C10—C11 | 121.6 (7) |
C4—N2—C3 | 134.1 (7) | C9—C10—H10 | 119.2 |
C1—N2—C3 | 108.0 (6) | C11—C10—H10 | 119.2 |
N1—C1—N2 | 117.7 (7) | C12—C11—C10 | 119.4 (7) |
N1—C1—S1 | 131.2 (7) | C12—C11—H11 | 120.3 |
N2—C1—S1 | 111.1 (5) | C10—C11—H11 | 120.3 |
N1—C2—C3 | 107.7 (6) | C11—C12—C13 | 121.3 (7) |
N1—C2—H2A | 110.2 | C11—C12—H12 | 119.4 |
C3—C2—H2A | 110.2 | C13—C12—H12 | 119.4 |
N1—C2—H2B | 110.2 | C14—C13—C8 | 121.6 (6) |
C3—C2—H2B | 110.2 | C14—C13—C12 | 120.0 (7) |
H2A—C2—H2B | 108.5 | C8—C13—C12 | 118.4 (6) |
N2—C3—C2 | 101.2 (6) | C13—C14—C15 | 120.8 (6) |
N2—C3—H3A | 111.5 | C13—C14—H14 | 119.6 |
C2—C3—H3A | 111.5 | C15—C14—H14 | 119.6 |
N2—C3—H3B | 111.5 | C14—C15—C16 | 122.3 (7) |
C2—C3—H3B | 111.5 | C14—C15—C20 | 119.1 (6) |
H3A—C3—H3B | 109.3 | C16—C15—C20 | 118.6 (7) |
O1—C4—N2 | 125.9 (7) | C17—C16—C15 | 122.0 (8) |
O1—C4—C5 | 124.6 (6) | C17—C16—H16 | 119.0 |
N2—C4—C5 | 109.4 (6) | C15—C16—H16 | 119.0 |
C6—C5—C4 | 123.5 (6) | C16—C17—C18 | 119.2 (8) |
C6—C5—S1 | 126.3 (5) | C16—C17—H17 | 120.4 |
C4—C5—S1 | 110.2 (5) | C18—C17—H17 | 120.4 |
C5—C6—C7 | 125.3 (6) | C19—C18—C17 | 121.1 (7) |
C5—C6—H6 | 117.3 | C19—C18—H18 | 119.5 |
C7—C6—H6 | 117.3 | C17—C18—H18 | 119.5 |
C20—C7—C8 | 119.7 (6) | C18—C19—C20 | 121.3 (7) |
C20—C7—C6 | 120.0 (5) | C18—C19—H19 | 119.4 |
C8—C7—C6 | 120.4 (6) | C20—C19—H19 | 119.4 |
C13—C8—C7 | 118.5 (6) | C7—C20—C19 | 121.9 (6) |
C13—C8—C9 | 119.3 (6) | C7—C20—C15 | 120.3 (6) |
C7—C8—C9 | 122.2 (6) | C19—C20—C15 | 117.9 (6) |
C10—C9—C8 | 119.9 (6) | | |
| | | |
C2—N1—C1—N2 | 2.0 (9) | C13—C8—C9—C10 | −0.7 (9) |
C2—N1—C1—S1 | −179.2 (6) | C7—C8—C9—C10 | −179.9 (6) |
C4—N2—C1—N1 | −176.2 (7) | C8—C9—C10—C11 | −2.2 (10) |
C3—N2—C1—N1 | −1.9 (9) | C9—C10—C11—C12 | 3.0 (11) |
C4—N2—C1—S1 | 4.8 (8) | C10—C11—C12—C13 | −0.8 (11) |
C3—N2—C1—S1 | 179.0 (5) | C7—C8—C13—C14 | 2.2 (9) |
C5—S1—C1—N1 | −179.9 (8) | C9—C8—C13—C14 | −177.1 (6) |
C5—S1—C1—N2 | −1.1 (5) | C7—C8—C13—C12 | −178.0 (6) |
C1—N1—C2—C3 | −1.3 (9) | C9—C8—C13—C12 | 2.8 (9) |
C4—N2—C3—C2 | 173.8 (8) | C11—C12—C13—C14 | 177.8 (7) |
C1—N2—C3—C2 | 0.8 (8) | C11—C12—C13—C8 | −2.0 (10) |
N1—C2—C3—N2 | 0.2 (8) | C8—C13—C14—C15 | −0.1 (10) |
C1—N2—C4—O1 | 173.7 (7) | C12—C13—C14—C15 | −179.9 (7) |
C3—N2—C4—O1 | 1.3 (14) | C13—C14—C15—C16 | 178.6 (6) |
C1—N2—C4—C5 | −6.4 (8) | C13—C14—C15—C20 | −0.8 (10) |
C3—N2—C4—C5 | −178.8 (7) | C14—C15—C16—C17 | −178.9 (8) |
O1—C4—C5—C6 | 3.4 (11) | C20—C15—C16—C17 | 0.5 (11) |
N2—C4—C5—C6 | −176.5 (7) | C15—C16—C17—C18 | −1.7 (12) |
O1—C4—C5—S1 | −174.9 (6) | C16—C17—C18—C19 | 1.4 (12) |
N2—C4—C5—S1 | 5.2 (7) | C17—C18—C19—C20 | 0.2 (11) |
C1—S1—C5—C6 | 179.4 (7) | C8—C7—C20—C19 | −178.4 (6) |
C1—S1—C5—C4 | −2.3 (5) | C6—C7—C20—C19 | 0.5 (9) |
C4—C5—C6—C7 | 179.8 (6) | C8—C7—C20—C15 | 2.4 (9) |
S1—C5—C6—C7 | −2.1 (10) | C6—C7—C20—C15 | −178.6 (6) |
C5—C6—C7—C20 | 119.6 (8) | C18—C19—C20—C7 | 179.4 (6) |
C5—C6—C7—C8 | −61.5 (9) | C18—C19—C20—C15 | −1.4 (10) |
C20—C7—C8—C13 | −3.3 (9) | C14—C15—C20—C7 | −0.4 (9) |
C6—C7—C8—C13 | 177.8 (6) | C16—C15—C20—C7 | −179.8 (6) |
C20—C7—C8—C9 | 175.9 (5) | C14—C15—C20—C19 | −179.5 (6) |
C6—C7—C8—C9 | −3.0 (9) | C16—C15—C20—C19 | 1.1 (9) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3A···O1i | 0.97 | 2.43 | 3.068 (10) | 123 |
Symmetry code: (i) x−1/2, −y−1/2, −z. |