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In the mol­ecule of the title compound, C24H21FN2O2S, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807012937/hk2216sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807012937/hk2216Isup2.hkl
Contains datablock I

CCDC reference: 647238

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](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

Computing details top

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
C23H21FN2O2SZ = 2
Mr = 408.48F(000) = 428
Triclinic, P1Dx = 1.376 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.6363 (11) ÅCell parameters from 390 reflections
b = 11.0660 (14) Åθ = 1.5–28.5°
c = 11.8153 (15) ŵ = 0.20 mm1
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 tube2256 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
φ and ω scansθmax = 25.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS;, Sheldrick, 1996)
h = 1010
Tmin = 0.943, Tmax = 0.965k = 1313
9977 measured reflectionsl = 1414
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)] = 0.070Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182H-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 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.19 e Å3
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
xyzUiso*/Ueq
F10.9235 (3)0.5757 (3)0.3689 (2)0.0947 (8)
N10.0098 (3)0.1310 (3)0.5498 (2)0.0462 (7)
N20.2507 (3)0.3389 (3)0.3921 (3)0.0553 (8)
H20.21830.27370.46020.066*
O10.1608 (4)0.4575 (3)0.2099 (3)0.1073 (13)
O20.2932 (3)0.0964 (3)1.0927 (2)0.0750 (8)
S10.29731 (11)0.07883 (10)0.44071 (9)0.0580 (3)
C10.0491 (4)0.0301 (4)0.6463 (3)0.0525 (9)
H10.15750.02320.64260.063*
C20.0886 (4)0.1663 (3)0.4468 (3)0.0458 (8)
C30.0400 (4)0.2737 (3)0.3384 (3)0.0465 (8)
C40.1683 (5)0.3965 (4)0.1262 (3)0.0613 (10)
H4A0.10890.48560.13180.074*
H4B0.10870.38070.07240.074*
C50.3372 (6)0.3971 (5)0.0723 (4)0.0927 (15)
H5A0.32740.44500.01530.111*
H5B0.37720.44930.10480.111*
C60.4594 (6)0.2645 (5)0.0936 (4)0.0950 (16)
H6A0.56410.27800.05970.114*
H6B0.42880.21720.05010.114*
C70.4810 (5)0.1736 (4)0.2277 (4)0.0674 (11)
H7A0.53140.07870.23430.081*
H7B0.55320.19850.26470.081*
C80.3182 (4)0.1893 (4)0.2943 (3)0.0525 (9)
C90.1745 (4)0.2876 (3)0.2519 (3)0.0489 (9)
C100.1312 (4)0.3658 (4)0.3080 (3)0.0544 (9)
C110.4218 (4)0.4042 (3)0.3828 (3)0.0482 (9)
C120.5232 (4)0.3437 (4)0.4707 (3)0.0584 (10)
H120.47720.26240.53380.070*
C130.6915 (5)0.4014 (4)0.4671 (4)0.0658 (11)
H130.75880.36040.52750.079*
C140.7573 (4)0.5193 (4)0.3736 (4)0.0613 (10)
C150.6611 (5)0.5807 (4)0.2855 (4)0.0645 (11)
H150.70910.66120.22230.077*
C160.4923 (4)0.5249 (4)0.2883 (3)0.0586 (10)
H160.42650.56760.22780.070*
C170.0408 (4)0.0071 (3)0.7611 (3)0.0469 (8)
C180.0367 (5)0.1140 (4)0.8624 (3)0.0628 (10)
H180.14520.16450.85420.075*
C190.0409 (5)0.1478 (4)0.9743 (3)0.0601 (10)
H190.01460.21971.04100.072*
C200.2023 (4)0.0740 (4)0.9871 (3)0.0534 (9)
C210.2830 (5)0.0313 (4)0.8863 (3)0.0640 (11)
H210.39250.08010.89400.077*
C220.2039 (4)0.0642 (4)0.7761 (3)0.0561 (10)
H220.25990.13580.70960.067*
C230.2185 (6)0.2059 (5)1.1990 (4)0.0870 (14)
H23A0.18060.29011.18290.130*
H23B0.29750.21331.26540.130*
H23C0.12720.18831.22040.130*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0435 (14)0.1005 (19)0.112 (2)0.0057 (12)0.0156 (13)0.0266 (16)
N10.0431 (16)0.0459 (17)0.0448 (17)0.0107 (13)0.0048 (14)0.0120 (14)
N20.0426 (17)0.0568 (19)0.0457 (17)0.0009 (14)0.0057 (14)0.0061 (14)
O10.0585 (19)0.113 (3)0.072 (2)0.0047 (17)0.0010 (15)0.0246 (19)
O20.0653 (18)0.081 (2)0.0496 (16)0.0107 (15)0.0039 (14)0.0034 (14)
S10.0413 (5)0.0590 (6)0.0580 (6)0.0062 (4)0.0028 (4)0.0108 (5)
C10.041 (2)0.052 (2)0.056 (2)0.0072 (17)0.0042 (17)0.0154 (18)
C20.0394 (19)0.047 (2)0.052 (2)0.0120 (16)0.0033 (16)0.0186 (18)
C30.047 (2)0.045 (2)0.047 (2)0.0123 (16)0.0047 (16)0.0159 (17)
C40.062 (3)0.065 (3)0.050 (2)0.019 (2)0.0014 (19)0.014 (2)
C50.078 (3)0.113 (4)0.061 (3)0.029 (3)0.008 (2)0.006 (3)
C60.072 (3)0.110 (4)0.082 (4)0.027 (3)0.027 (3)0.022 (3)
C70.047 (2)0.081 (3)0.070 (3)0.017 (2)0.010 (2)0.027 (2)
C80.049 (2)0.058 (2)0.050 (2)0.0189 (18)0.0002 (17)0.0170 (18)
C90.047 (2)0.052 (2)0.046 (2)0.0161 (18)0.0016 (16)0.0147 (17)
C100.051 (2)0.056 (2)0.044 (2)0.0081 (18)0.0055 (18)0.0105 (19)
C110.042 (2)0.051 (2)0.047 (2)0.0023 (17)0.0090 (16)0.0198 (17)
C120.049 (2)0.059 (2)0.053 (2)0.0083 (19)0.0071 (18)0.0084 (19)
C130.046 (2)0.075 (3)0.067 (3)0.011 (2)0.003 (2)0.020 (2)
C140.038 (2)0.067 (3)0.074 (3)0.001 (2)0.011 (2)0.029 (2)
C150.060 (3)0.051 (2)0.066 (3)0.000 (2)0.020 (2)0.011 (2)
C160.050 (2)0.053 (2)0.058 (2)0.0049 (18)0.0051 (18)0.0124 (19)
C170.041 (2)0.047 (2)0.048 (2)0.0104 (16)0.0039 (16)0.0143 (17)
C180.043 (2)0.064 (3)0.059 (2)0.0029 (18)0.0049 (18)0.008 (2)
C190.055 (2)0.059 (2)0.047 (2)0.0098 (19)0.0118 (19)0.0002 (18)
C200.052 (2)0.053 (2)0.050 (2)0.0165 (18)0.0026 (18)0.0113 (18)
C210.050 (2)0.065 (3)0.056 (2)0.0029 (19)0.0012 (19)0.010 (2)
C220.054 (2)0.051 (2)0.047 (2)0.0050 (18)0.0092 (18)0.0061 (17)
C230.099 (4)0.082 (3)0.057 (3)0.026 (3)0.005 (2)0.003 (2)
Geometric parameters (Å, º) top
F1—C141.360 (4)C7—H7A0.9700
N1—C11.279 (4)C7—H7B0.9700
N1—C21.386 (4)C8—C91.357 (5)
N2—C101.351 (4)C11—C121.378 (5)
N2—C111.411 (4)C11—C161.389 (5)
N2—H20.8600C12—C131.378 (5)
O1—C101.210 (4)C12—H120.9300
O2—C201.359 (4)C13—C141.359 (5)
O2—C231.424 (5)C13—H130.9300
S1—C81.727 (4)C14—C151.352 (6)
S1—C21.743 (3)C15—C161.380 (5)
C1—C171.449 (5)C15—H150.9300
C1—H10.9300C16—H160.9300
C2—C31.380 (4)C17—C181.384 (5)
C3—C91.440 (5)C17—C221.388 (5)
C3—C101.492 (5)C18—C191.369 (5)
C4—C91.514 (5)C18—H180.9300
C4—C51.505 (6)C19—C201.380 (5)
C4—H4A0.9700C19—H190.9300
C4—H4B0.9700C20—C211.384 (5)
C5—C61.447 (6)C21—C221.358 (5)
C5—H5A0.9700C21—H210.9300
C5—H5B0.9700C22—H220.9300
C6—C71.522 (6)C23—H23A0.9600
C6—H6A0.9700C23—H23B0.9600
C6—H6B0.9700C23—H23C0.9600
C7—C81.498 (5)
C1—N1—C2120.9 (3)O1—C10—N2122.1 (3)
C10—N2—C11128.4 (3)O1—C10—C3120.6 (3)
C10—N2—H2115.8N2—C10—C3117.3 (3)
C11—N2—H2115.8C12—C11—C16118.7 (3)
C20—O2—C23118.2 (3)C12—C11—N2118.2 (3)
C8—S1—C291.67 (17)C16—C11—N2123.1 (3)
N1—C1—C17124.7 (3)C11—C12—C13121.3 (3)
N1—C1—H1117.6C11—C12—H12119.3
C17—C1—H1117.6C13—C12—H12119.3
N1—C2—C3126.3 (3)C14—C13—C12118.8 (4)
N1—C2—S1122.8 (2)C14—C13—H13120.6
C3—C2—S1110.9 (3)C12—C13—H13120.6
C2—C3—C9112.4 (3)C15—C14—F1119.7 (4)
C2—C3—C10125.9 (3)C15—C14—C13121.3 (3)
C9—C3—C10121.7 (3)F1—C14—C13118.9 (4)
C9—C4—C5112.2 (3)C14—C15—C16120.6 (4)
C9—C4—H4A109.2C14—C15—H15119.7
C5—C4—H4A109.2C16—C15—H15119.7
C9—C4—H4B109.2C11—C16—C15119.2 (4)
C5—C4—H4B109.2C11—C16—H16120.4
H4A—C4—H4B107.9C15—C16—H16120.4
C6—C5—C4116.3 (4)C18—C17—C22117.3 (3)
C6—C5—H5A108.2C18—C17—C1120.3 (3)
C4—C5—H5A108.2C22—C17—C1122.4 (3)
C6—C5—H5B108.2C19—C18—C17122.3 (3)
C4—C5—H5B108.2C19—C18—H18118.9
H5A—C5—H5B107.4C17—C18—H18118.9
C5—C6—C7114.2 (4)C18—C19—C20119.2 (3)
C5—C6—H6A108.7C18—C19—H19120.4
C7—C6—H6A108.7C20—C19—H19120.4
C5—C6—H6B108.7O2—C20—C19125.2 (3)
C7—C6—H6B108.7O2—C20—C21115.5 (3)
H6A—C6—H6B107.6C19—C20—C21119.3 (3)
C8—C7—C6110.5 (3)C22—C21—C20120.7 (4)
C8—C7—H7A109.6C22—C21—H21119.7
C6—C7—H7A109.6C20—C21—H21119.7
C8—C7—H7B109.6C21—C22—C17121.2 (3)
C6—C7—H7B109.6C21—C22—H22119.4
H7A—C7—H7B108.1C17—C22—H22119.4
C9—C8—C7126.4 (3)O2—C23—H23A109.5
C9—C8—S1112.3 (3)O2—C23—H23B109.5
C7—C8—S1121.3 (3)H23A—C23—H23B109.5
C8—C9—C3112.6 (3)O2—C23—H23C109.5
C8—C9—C4120.3 (3)H23A—C23—H23C109.5
C3—C9—C4127.1 (3)H23B—C23—H23C109.5
C2—N1—C1—C17174.6 (3)C9—C3—C10—O12.0 (6)
C1—N1—C2—C3179.0 (3)C2—C3—C10—N22.5 (5)
C1—N1—C2—S10.5 (4)C9—C3—C10—N2175.7 (3)
C8—S1—C2—N1177.4 (3)C10—N2—C11—C12168.1 (4)
C8—S1—C2—C31.3 (3)C10—N2—C11—C1610.9 (6)
N1—C2—C3—C9176.5 (3)C16—C11—C12—C130.7 (6)
S1—C2—C3—C92.1 (4)N2—C11—C12—C13179.7 (3)
N1—C2—C3—C105.1 (5)C11—C12—C13—C140.8 (6)
S1—C2—C3—C10176.2 (3)C12—C13—C14—C150.4 (6)
C9—C4—C5—C639.2 (6)C12—C13—C14—F1179.2 (3)
C4—C5—C6—C754.6 (6)F1—C14—C15—C16179.8 (3)
C5—C6—C7—C838.5 (6)C13—C14—C15—C160.2 (6)
C6—C7—C8—C912.3 (6)C12—C11—C16—C150.1 (5)
C6—C7—C8—S1168.7 (3)N2—C11—C16—C15179.1 (3)
C2—S1—C8—C90.0 (3)C14—C15—C16—C110.3 (6)
C2—S1—C8—C7179.1 (3)N1—C1—C17—C18176.6 (3)
C7—C8—C9—C3179.8 (3)N1—C1—C17—C221.0 (6)
S1—C8—C9—C31.2 (4)C22—C17—C18—C191.3 (6)
C7—C8—C9—C40.6 (6)C1—C17—C18—C19176.3 (4)
S1—C8—C9—C4178.5 (3)C17—C18—C19—C200.5 (6)
C2—C3—C9—C82.1 (4)C23—O2—C20—C191.2 (6)
C10—C3—C9—C8176.3 (3)C23—O2—C20—C21178.3 (4)
C2—C3—C9—C4177.5 (3)C18—C19—C20—O2179.7 (4)
C10—C3—C9—C44.1 (5)C18—C19—C20—C210.9 (6)
C5—C4—C9—C811.6 (5)O2—C20—C21—C22179.2 (4)
C5—C4—C9—C3168.0 (4)C19—C20—C21—C221.4 (6)
C11—N2—C10—O12.0 (6)C20—C21—C22—C170.5 (6)
C11—N2—C10—C3175.6 (3)C18—C17—C22—C210.8 (6)
C2—C3—C10—O1179.8 (4)C1—C17—C22—C21176.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···N10.862.062.791 (4)142
C1—H1···S10.932.543.010 (4)111
C5—H5A···O1i0.972.563.438 (6)150
C16—H16···O10.932.232.817 (5)120
Symmetry code: (i) x, y+1, z.
 

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