In the molecule of the title compound, C
24H
21FN
2O
2S, the fused six-membered ring has a half-chair conformation, with a pseudo-twofold axis passing through the mid-points of the bridgehead C—C bond and the opposite C—C bond. The dihedral angles between the planar thiophene (
B), fluorophenyl (
C) and methoxyphenyl (
D) rings are
B/
C = 13.65 (3)°,
B/
D = 9.72 (2)° and
C/
D = 23.34 (3)°. In the crystal structure, intermolecular C—H
O hydrogen bonds link the molecules into centrosymmetric dimers; these may be effective in the stabilization of the structure.
Supporting information
CCDC reference: 647238
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.005 Å
- R factor = 0.070
- wR factor = 0.182
- Data-to-parameter ratio = 13.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C23 H21 F N2 O2 S
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 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
0 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
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A
PUBL022_ALERT_1_A There is a mismatched ~ on line 148
In the molecule of the title compound, C~24~H~21~F~N~2~O~2~S, the fused
If you require a ~ then it should be escaped
with a \, i.e. \~
Otherwise there must be a matching closing ~, e.g. C~2~H~4~
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PARST (Nardelli, 1995) and PLATON (Spek, 2003).
N-(4-Fluorophenyl)-2-{[(1E)-(4-methoxyphenyl)methylene]amino}-4,5,6,7-
tetrahydro-1-benzothiophene-3-carboxamide
top
Crystal data top
C23H21FN2O2S | Z = 2 |
Mr = 408.48 | F(000) = 428 |
Triclinic, P1 | Dx = 1.376 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.6363 (11) Å | Cell parameters from 390 reflections |
b = 11.0660 (14) Å | θ = 1.5–28.5° |
c = 11.8153 (15) Å | µ = 0.20 mm−1 |
α = 67.874 (3)° | T = 291 K |
β = 81.656 (2)° | Block, brown |
γ = 70.473 (2)° | 0.32 × 0.26 × 0.19 mm |
V = 985.6 (2) Å3 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3656 independent reflections |
Radiation source: fine-focus sealed tube | 2256 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
φ and ω scans | θmax = 25.5°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS;, Sheldrick, 1996) | h = −10→10 |
Tmin = 0.943, Tmax = 0.965 | k = −13→13 |
9977 measured reflections | l = −14→14 |
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)] = 0.070 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.182 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0916P)2 + 0.2792P] where P = (Fo2 + 2Fc2)/3 |
3656 reflections | (Δ/σ)max < 0.001 |
263 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.19 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 | |
F1 | −0.9235 (3) | 0.5757 (3) | 0.3689 (2) | 0.0947 (8) | |
N1 | −0.0098 (3) | 0.1310 (3) | 0.5498 (2) | 0.0462 (7) | |
N2 | −0.2507 (3) | 0.3389 (3) | 0.3921 (3) | 0.0553 (8) | |
H2 | −0.2183 | 0.2737 | 0.4602 | 0.066* | |
O1 | −0.1608 (4) | 0.4575 (3) | 0.2099 (3) | 0.1073 (13) | |
O2 | −0.2932 (3) | −0.0964 (3) | 1.0927 (2) | 0.0750 (8) | |
S1 | 0.29731 (11) | 0.07883 (10) | 0.44071 (9) | 0.0580 (3) | |
C1 | 0.0491 (4) | 0.0301 (4) | 0.6463 (3) | 0.0525 (9) | |
H1 | 0.1575 | −0.0232 | 0.6426 | 0.063* | |
C2 | 0.0886 (4) | 0.1663 (3) | 0.4468 (3) | 0.0458 (8) | |
C3 | 0.0400 (4) | 0.2737 (3) | 0.3384 (3) | 0.0465 (8) | |
C4 | 0.1683 (5) | 0.3965 (4) | 0.1262 (3) | 0.0613 (10) | |
H4A | 0.1089 | 0.4856 | 0.1318 | 0.074* | |
H4B | 0.1087 | 0.3807 | 0.0724 | 0.074* | |
C5 | 0.3372 (6) | 0.3971 (5) | 0.0723 (4) | 0.0927 (15) | |
H5A | 0.3274 | 0.4450 | −0.0153 | 0.111* | |
H5B | 0.3772 | 0.4493 | 0.1048 | 0.111* | |
C6 | 0.4594 (6) | 0.2645 (5) | 0.0936 (4) | 0.0950 (16) | |
H6A | 0.5641 | 0.2780 | 0.0597 | 0.114* | |
H6B | 0.4288 | 0.2172 | 0.0501 | 0.114* | |
C7 | 0.4810 (5) | 0.1736 (4) | 0.2277 (4) | 0.0674 (11) | |
H7A | 0.5314 | 0.0787 | 0.2343 | 0.081* | |
H7B | 0.5532 | 0.1985 | 0.2647 | 0.081* | |
C8 | 0.3182 (4) | 0.1893 (4) | 0.2943 (3) | 0.0525 (9) | |
C9 | 0.1745 (4) | 0.2876 (3) | 0.2519 (3) | 0.0489 (9) | |
C10 | −0.1312 (4) | 0.3658 (4) | 0.3080 (3) | 0.0544 (9) | |
C11 | −0.4218 (4) | 0.4042 (3) | 0.3828 (3) | 0.0482 (9) | |
C12 | −0.5232 (4) | 0.3437 (4) | 0.4707 (3) | 0.0584 (10) | |
H12 | −0.4772 | 0.2624 | 0.5338 | 0.070* | |
C13 | −0.6915 (5) | 0.4014 (4) | 0.4671 (4) | 0.0658 (11) | |
H13 | −0.7588 | 0.3604 | 0.5275 | 0.079* | |
C14 | −0.7573 (4) | 0.5193 (4) | 0.3736 (4) | 0.0613 (10) | |
C15 | −0.6611 (5) | 0.5807 (4) | 0.2855 (4) | 0.0645 (11) | |
H15 | −0.7091 | 0.6612 | 0.2223 | 0.077* | |
C16 | −0.4923 (4) | 0.5249 (4) | 0.2883 (3) | 0.0586 (10) | |
H16 | −0.4265 | 0.5676 | 0.2278 | 0.070* | |
C17 | −0.0408 (4) | −0.0071 (3) | 0.7611 (3) | 0.0469 (8) | |
C18 | 0.0367 (5) | −0.1140 (4) | 0.8624 (3) | 0.0628 (10) | |
H18 | 0.1452 | −0.1645 | 0.8542 | 0.075* | |
C19 | −0.0409 (5) | −0.1478 (4) | 0.9743 (3) | 0.0601 (10) | |
H19 | 0.0146 | −0.2197 | 1.0410 | 0.072* | |
C20 | −0.2023 (4) | −0.0740 (4) | 0.9871 (3) | 0.0534 (9) | |
C21 | −0.2830 (5) | 0.0313 (4) | 0.8863 (3) | 0.0640 (11) | |
H21 | −0.3925 | 0.0801 | 0.8940 | 0.077* | |
C22 | −0.2039 (4) | 0.0642 (4) | 0.7761 (3) | 0.0561 (10) | |
H22 | −0.2599 | 0.1358 | 0.7096 | 0.067* | |
C23 | −0.2185 (6) | −0.2059 (5) | 1.1990 (4) | 0.0870 (14) | |
H23A | −0.1806 | −0.2901 | 1.1829 | 0.130* | |
H23B | −0.2975 | −0.2133 | 1.2654 | 0.130* | |
H23C | −0.1272 | −0.1883 | 1.2204 | 0.130* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1 | 0.0435 (14) | 0.1005 (19) | 0.112 (2) | 0.0057 (12) | −0.0156 (13) | −0.0266 (16) |
N1 | 0.0431 (16) | 0.0459 (17) | 0.0448 (17) | −0.0107 (13) | −0.0048 (14) | −0.0120 (14) |
N2 | 0.0426 (17) | 0.0568 (19) | 0.0457 (17) | −0.0009 (14) | −0.0057 (14) | −0.0061 (14) |
O1 | 0.0585 (19) | 0.113 (3) | 0.072 (2) | 0.0047 (17) | 0.0010 (15) | 0.0246 (19) |
O2 | 0.0653 (18) | 0.081 (2) | 0.0496 (16) | −0.0107 (15) | 0.0039 (14) | −0.0034 (14) |
S1 | 0.0413 (5) | 0.0590 (6) | 0.0580 (6) | −0.0062 (4) | −0.0028 (4) | −0.0108 (5) |
C1 | 0.041 (2) | 0.052 (2) | 0.056 (2) | −0.0072 (17) | −0.0042 (17) | −0.0154 (18) |
C2 | 0.0394 (19) | 0.047 (2) | 0.052 (2) | −0.0120 (16) | −0.0033 (16) | −0.0186 (18) |
C3 | 0.047 (2) | 0.045 (2) | 0.047 (2) | −0.0123 (16) | −0.0047 (16) | −0.0159 (17) |
C4 | 0.062 (3) | 0.065 (3) | 0.050 (2) | −0.019 (2) | 0.0014 (19) | −0.014 (2) |
C5 | 0.078 (3) | 0.113 (4) | 0.061 (3) | −0.029 (3) | 0.008 (2) | −0.006 (3) |
C6 | 0.072 (3) | 0.110 (4) | 0.082 (4) | −0.027 (3) | 0.027 (3) | −0.022 (3) |
C7 | 0.047 (2) | 0.081 (3) | 0.070 (3) | −0.017 (2) | 0.010 (2) | −0.027 (2) |
C8 | 0.049 (2) | 0.058 (2) | 0.050 (2) | −0.0189 (18) | 0.0002 (17) | −0.0170 (18) |
C9 | 0.047 (2) | 0.052 (2) | 0.046 (2) | −0.0161 (18) | −0.0016 (16) | −0.0147 (17) |
C10 | 0.051 (2) | 0.056 (2) | 0.044 (2) | −0.0081 (18) | −0.0055 (18) | −0.0105 (19) |
C11 | 0.042 (2) | 0.051 (2) | 0.047 (2) | −0.0023 (17) | −0.0090 (16) | −0.0198 (17) |
C12 | 0.049 (2) | 0.059 (2) | 0.053 (2) | −0.0083 (19) | −0.0071 (18) | −0.0084 (19) |
C13 | 0.046 (2) | 0.075 (3) | 0.067 (3) | −0.011 (2) | −0.003 (2) | −0.020 (2) |
C14 | 0.038 (2) | 0.067 (3) | 0.074 (3) | −0.001 (2) | −0.011 (2) | −0.029 (2) |
C15 | 0.060 (3) | 0.051 (2) | 0.066 (3) | 0.000 (2) | −0.020 (2) | −0.011 (2) |
C16 | 0.050 (2) | 0.053 (2) | 0.058 (2) | −0.0049 (18) | −0.0051 (18) | −0.0124 (19) |
C17 | 0.041 (2) | 0.047 (2) | 0.048 (2) | −0.0104 (16) | −0.0039 (16) | −0.0143 (17) |
C18 | 0.043 (2) | 0.064 (3) | 0.059 (2) | −0.0029 (18) | −0.0049 (18) | −0.008 (2) |
C19 | 0.055 (2) | 0.059 (2) | 0.047 (2) | −0.0098 (19) | −0.0118 (19) | −0.0002 (18) |
C20 | 0.052 (2) | 0.053 (2) | 0.050 (2) | −0.0165 (18) | −0.0026 (18) | −0.0113 (18) |
C21 | 0.050 (2) | 0.065 (3) | 0.056 (2) | −0.0029 (19) | −0.0012 (19) | −0.010 (2) |
C22 | 0.054 (2) | 0.051 (2) | 0.047 (2) | −0.0050 (18) | −0.0092 (18) | −0.0061 (17) |
C23 | 0.099 (4) | 0.082 (3) | 0.057 (3) | −0.026 (3) | 0.005 (2) | −0.003 (2) |
Geometric parameters (Å, º) top
F1—C14 | 1.360 (4) | C7—H7A | 0.9700 |
N1—C1 | 1.279 (4) | C7—H7B | 0.9700 |
N1—C2 | 1.386 (4) | C8—C9 | 1.357 (5) |
N2—C10 | 1.351 (4) | C11—C12 | 1.378 (5) |
N2—C11 | 1.411 (4) | C11—C16 | 1.389 (5) |
N2—H2 | 0.8600 | C12—C13 | 1.378 (5) |
O1—C10 | 1.210 (4) | C12—H12 | 0.9300 |
O2—C20 | 1.359 (4) | C13—C14 | 1.359 (5) |
O2—C23 | 1.424 (5) | C13—H13 | 0.9300 |
S1—C8 | 1.727 (4) | C14—C15 | 1.352 (6) |
S1—C2 | 1.743 (3) | C15—C16 | 1.380 (5) |
C1—C17 | 1.449 (5) | C15—H15 | 0.9300 |
C1—H1 | 0.9300 | C16—H16 | 0.9300 |
C2—C3 | 1.380 (4) | C17—C18 | 1.384 (5) |
C3—C9 | 1.440 (5) | C17—C22 | 1.388 (5) |
C3—C10 | 1.492 (5) | C18—C19 | 1.369 (5) |
C4—C9 | 1.514 (5) | C18—H18 | 0.9300 |
C4—C5 | 1.505 (6) | C19—C20 | 1.380 (5) |
C4—H4A | 0.9700 | C19—H19 | 0.9300 |
C4—H4B | 0.9700 | C20—C21 | 1.384 (5) |
C5—C6 | 1.447 (6) | C21—C22 | 1.358 (5) |
C5—H5A | 0.9700 | C21—H21 | 0.9300 |
C5—H5B | 0.9700 | C22—H22 | 0.9300 |
C6—C7 | 1.522 (6) | C23—H23A | 0.9600 |
C6—H6A | 0.9700 | C23—H23B | 0.9600 |
C6—H6B | 0.9700 | C23—H23C | 0.9600 |
C7—C8 | 1.498 (5) | | |
| | | |
C1—N1—C2 | 120.9 (3) | O1—C10—N2 | 122.1 (3) |
C10—N2—C11 | 128.4 (3) | O1—C10—C3 | 120.6 (3) |
C10—N2—H2 | 115.8 | N2—C10—C3 | 117.3 (3) |
C11—N2—H2 | 115.8 | C12—C11—C16 | 118.7 (3) |
C20—O2—C23 | 118.2 (3) | C12—C11—N2 | 118.2 (3) |
C8—S1—C2 | 91.67 (17) | C16—C11—N2 | 123.1 (3) |
N1—C1—C17 | 124.7 (3) | C11—C12—C13 | 121.3 (3) |
N1—C1—H1 | 117.6 | C11—C12—H12 | 119.3 |
C17—C1—H1 | 117.6 | C13—C12—H12 | 119.3 |
N1—C2—C3 | 126.3 (3) | C14—C13—C12 | 118.8 (4) |
N1—C2—S1 | 122.8 (2) | C14—C13—H13 | 120.6 |
C3—C2—S1 | 110.9 (3) | C12—C13—H13 | 120.6 |
C2—C3—C9 | 112.4 (3) | C15—C14—F1 | 119.7 (4) |
C2—C3—C10 | 125.9 (3) | C15—C14—C13 | 121.3 (3) |
C9—C3—C10 | 121.7 (3) | F1—C14—C13 | 118.9 (4) |
C9—C4—C5 | 112.2 (3) | C14—C15—C16 | 120.6 (4) |
C9—C4—H4A | 109.2 | C14—C15—H15 | 119.7 |
C5—C4—H4A | 109.2 | C16—C15—H15 | 119.7 |
C9—C4—H4B | 109.2 | C11—C16—C15 | 119.2 (4) |
C5—C4—H4B | 109.2 | C11—C16—H16 | 120.4 |
H4A—C4—H4B | 107.9 | C15—C16—H16 | 120.4 |
C6—C5—C4 | 116.3 (4) | C18—C17—C22 | 117.3 (3) |
C6—C5—H5A | 108.2 | C18—C17—C1 | 120.3 (3) |
C4—C5—H5A | 108.2 | C22—C17—C1 | 122.4 (3) |
C6—C5—H5B | 108.2 | C19—C18—C17 | 122.3 (3) |
C4—C5—H5B | 108.2 | C19—C18—H18 | 118.9 |
H5A—C5—H5B | 107.4 | C17—C18—H18 | 118.9 |
C5—C6—C7 | 114.2 (4) | C18—C19—C20 | 119.2 (3) |
C5—C6—H6A | 108.7 | C18—C19—H19 | 120.4 |
C7—C6—H6A | 108.7 | C20—C19—H19 | 120.4 |
C5—C6—H6B | 108.7 | O2—C20—C19 | 125.2 (3) |
C7—C6—H6B | 108.7 | O2—C20—C21 | 115.5 (3) |
H6A—C6—H6B | 107.6 | C19—C20—C21 | 119.3 (3) |
C8—C7—C6 | 110.5 (3) | C22—C21—C20 | 120.7 (4) |
C8—C7—H7A | 109.6 | C22—C21—H21 | 119.7 |
C6—C7—H7A | 109.6 | C20—C21—H21 | 119.7 |
C8—C7—H7B | 109.6 | C21—C22—C17 | 121.2 (3) |
C6—C7—H7B | 109.6 | C21—C22—H22 | 119.4 |
H7A—C7—H7B | 108.1 | C17—C22—H22 | 119.4 |
C9—C8—C7 | 126.4 (3) | O2—C23—H23A | 109.5 |
C9—C8—S1 | 112.3 (3) | O2—C23—H23B | 109.5 |
C7—C8—S1 | 121.3 (3) | H23A—C23—H23B | 109.5 |
C8—C9—C3 | 112.6 (3) | O2—C23—H23C | 109.5 |
C8—C9—C4 | 120.3 (3) | H23A—C23—H23C | 109.5 |
C3—C9—C4 | 127.1 (3) | H23B—C23—H23C | 109.5 |
| | | |
C2—N1—C1—C17 | 174.6 (3) | C9—C3—C10—O1 | −2.0 (6) |
C1—N1—C2—C3 | −179.0 (3) | C2—C3—C10—N2 | −2.5 (5) |
C1—N1—C2—S1 | −0.5 (4) | C9—C3—C10—N2 | 175.7 (3) |
C8—S1—C2—N1 | −177.4 (3) | C10—N2—C11—C12 | 168.1 (4) |
C8—S1—C2—C3 | 1.3 (3) | C10—N2—C11—C16 | −10.9 (6) |
N1—C2—C3—C9 | 176.5 (3) | C16—C11—C12—C13 | −0.7 (6) |
S1—C2—C3—C9 | −2.1 (4) | N2—C11—C12—C13 | −179.7 (3) |
N1—C2—C3—C10 | −5.1 (5) | C11—C12—C13—C14 | 0.8 (6) |
S1—C2—C3—C10 | 176.2 (3) | C12—C13—C14—C15 | −0.4 (6) |
C9—C4—C5—C6 | 39.2 (6) | C12—C13—C14—F1 | 179.2 (3) |
C4—C5—C6—C7 | −54.6 (6) | F1—C14—C15—C16 | −179.8 (3) |
C5—C6—C7—C8 | 38.5 (6) | C13—C14—C15—C16 | −0.2 (6) |
C6—C7—C8—C9 | −12.3 (6) | C12—C11—C16—C15 | 0.1 (5) |
C6—C7—C8—S1 | 168.7 (3) | N2—C11—C16—C15 | 179.1 (3) |
C2—S1—C8—C9 | 0.0 (3) | C14—C15—C16—C11 | 0.3 (6) |
C2—S1—C8—C7 | 179.1 (3) | N1—C1—C17—C18 | −176.6 (3) |
C7—C8—C9—C3 | 179.8 (3) | N1—C1—C17—C22 | 1.0 (6) |
S1—C8—C9—C3 | −1.2 (4) | C22—C17—C18—C19 | −1.3 (6) |
C7—C8—C9—C4 | −0.6 (6) | C1—C17—C18—C19 | 176.3 (4) |
S1—C8—C9—C4 | 178.5 (3) | C17—C18—C19—C20 | 0.5 (6) |
C2—C3—C9—C8 | 2.1 (4) | C23—O2—C20—C19 | −1.2 (6) |
C10—C3—C9—C8 | −176.3 (3) | C23—O2—C20—C21 | 178.3 (4) |
C2—C3—C9—C4 | −177.5 (3) | C18—C19—C20—O2 | −179.7 (4) |
C10—C3—C9—C4 | 4.1 (5) | C18—C19—C20—C21 | 0.9 (6) |
C5—C4—C9—C8 | −11.6 (5) | O2—C20—C21—C22 | 179.2 (4) |
C5—C4—C9—C3 | 168.0 (4) | C19—C20—C21—C22 | −1.4 (6) |
C11—N2—C10—O1 | 2.0 (6) | C20—C21—C22—C17 | 0.5 (6) |
C11—N2—C10—C3 | −175.6 (3) | C18—C17—C22—C21 | 0.8 (6) |
C2—C3—C10—O1 | 179.8 (4) | C1—C17—C22—C21 | −176.8 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···N1 | 0.86 | 2.06 | 2.791 (4) | 142 |
C1—H1···S1 | 0.93 | 2.54 | 3.010 (4) | 111 |
C5—H5A···O1i | 0.97 | 2.56 | 3.438 (6) | 150 |
C16—H16···O1 | 0.93 | 2.23 | 2.817 (5) | 120 |
Symmetry code: (i) −x, −y+1, −z. |