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The title compound, C20H17FN2, has been synthesized by the reductive cyclization induced by a low-valent titanium reagent. The cyclo­pentene ring adopts an envelope conformation, while the partially saturated six-membered ring adopts a distorted half-chair conformation. Intermolecular N—H...N hydrogen bonds between the amino and cyano groups result in the formation of a dimer structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803020798/ob6305sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803020798/ob6305Isup2.hkl
Contains datablock I

CCDC reference: 225789

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.038
  • wR factor = 0.091
  • Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C8 - C20 = 8.41 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C13 - C14 = 8.31 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C16 - C17 = 8.94 su
Alert level C PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C3 PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1B ... ?
0 ALERT level A = In general: serious problem 3 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 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

3-Amino-1-(4-fluorophenyl)-3a,3 b,6,7-tetrahydrobenzo[4,5]indene-2-carbonitrile top
Crystal data top
C20H17FN2F(000) = 640
Mr = 304.36Dx = 1.249 Mg m3
Monoclinic, P21/nMelting point = 472–473 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 11.516 (2) ÅCell parameters from 30 reflections
b = 9.710 (1) Åθ = 2.9–14.4°
c = 14.914 (2) ŵ = 0.08 mm1
β = 103.97 (1)°T = 291 K
V = 1618.4 (4) Å3Block, colorless
Z = 40.52 × 0.42 × 0.30 mm
Data collection top
Siemens P4
diffractometer
Rint = 0.009
Radiation source: normal-focus sealed tubeθmax = 25.5°, θmin = 2.0°
Graphite monochromatorh = 013
ω scansk = 011
3487 measured reflectionsl = 1817
3005 independent reflections3 standard reflections every 97 reflections
1534 reflections with I > 2σ(I) intensity decay: 2.9%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.091 w = 1/[σ2(Fo2) + (0.0443P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.83(Δ/σ)max < 0.001
3005 reflectionsΔρmax = 0.12 e Å3
209 parametersΔρmin = 0.09 e Å3
0 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0113 (12)
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
F0.55958 (12)0.56213 (13)0.10083 (8)0.1177 (5)
N10.32501 (13)0.17485 (15)0.55782 (10)0.0807 (5)
H1A0.38190.11520.56650.097*
H1B0.28570.18740.59940.097*
N20.50964 (16)0.0696 (2)0.39359 (12)0.1024 (6)
C10.31100 (16)0.41981 (17)0.17674 (12)0.0674 (5)
H10.23160.39560.15180.081*
C20.3779 (2)0.47465 (19)0.11946 (13)0.0786 (6)
H20.34470.48610.05660.094*
C30.4929 (2)0.51117 (19)0.15768 (16)0.0779 (6)
C40.54439 (18)0.4964 (2)0.24833 (15)0.0846 (6)
H40.62320.52350.27260.102*
C50.47689 (17)0.4397 (2)0.30476 (13)0.0772 (5)
H50.51160.42810.36740.093*
C60.35956 (16)0.40037 (17)0.26997 (11)0.0594 (5)
C70.28426 (15)0.33778 (18)0.32966 (11)0.0624 (5)
H70.22110.28360.28900.075*
C80.34837 (14)0.24344 (18)0.40675 (11)0.0610 (5)
C90.29754 (15)0.24840 (18)0.47928 (11)0.0608 (4)
C100.19256 (14)0.34703 (17)0.45904 (11)0.0605 (5)
H100.12130.29350.42990.073*
C110.22250 (15)0.43921 (18)0.38362 (11)0.0621 (5)
H110.14860.47470.34300.075*
C120.30073 (16)0.55799 (18)0.42890 (12)0.0713 (5)
H12A0.31970.61630.38160.086*
H12B0.37520.52220.46680.086*
C130.23723 (17)0.64316 (19)0.48891 (13)0.0792 (6)
H13A0.29280.71090.52280.095*
H13B0.17130.69250.44910.095*
C140.18961 (15)0.5582 (2)0.55654 (12)0.0698 (5)
C150.16320 (17)0.6195 (2)0.63399 (14)0.0871 (6)
H150.17840.71280.64510.104*
C160.11502 (18)0.5436 (3)0.69408 (14)0.0952 (7)
H160.09890.58580.74570.114*
C170.09061 (18)0.4068 (3)0.67860 (15)0.0912 (7)
H170.05840.35560.71940.109*
C180.11431 (16)0.3463 (2)0.60208 (13)0.0792 (6)
H180.09560.25380.59040.095*
C190.16579 (14)0.41953 (19)0.54108 (12)0.0636 (5)
C200.43796 (18)0.1485 (2)0.39943 (12)0.0728 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F0.1610 (12)0.1039 (10)0.1118 (9)0.0299 (9)0.0787 (9)0.0055 (8)
N10.0949 (11)0.0819 (11)0.0768 (10)0.0396 (9)0.0430 (9)0.0244 (9)
N20.1227 (15)0.0974 (14)0.1077 (13)0.0522 (12)0.0679 (12)0.0289 (11)
C10.0797 (12)0.0605 (11)0.0622 (11)0.0032 (10)0.0176 (10)0.0044 (10)
C20.1215 (18)0.0591 (12)0.0581 (12)0.0008 (13)0.0275 (13)0.0040 (10)
C30.1061 (17)0.0626 (13)0.0776 (15)0.0048 (12)0.0469 (14)0.0016 (11)
C40.0761 (13)0.0939 (16)0.0889 (16)0.0013 (12)0.0300 (12)0.0057 (12)
C50.0674 (12)0.0973 (15)0.0683 (12)0.0072 (12)0.0189 (10)0.0129 (11)
C60.0627 (11)0.0600 (11)0.0578 (11)0.0105 (9)0.0187 (9)0.0036 (9)
C70.0600 (10)0.0697 (12)0.0601 (10)0.0055 (9)0.0193 (9)0.0030 (9)
C80.0642 (11)0.0590 (11)0.0653 (10)0.0157 (9)0.0266 (9)0.0062 (9)
C90.0671 (11)0.0539 (10)0.0653 (11)0.0120 (9)0.0235 (9)0.0066 (9)
C100.0571 (10)0.0630 (11)0.0651 (11)0.0107 (9)0.0219 (9)0.0030 (9)
C110.0586 (10)0.0667 (11)0.0617 (11)0.0140 (10)0.0156 (9)0.0079 (10)
C120.0763 (12)0.0623 (12)0.0799 (12)0.0116 (11)0.0279 (10)0.0111 (10)
C130.0850 (14)0.0628 (12)0.0892 (14)0.0185 (11)0.0203 (11)0.0011 (11)
C140.0685 (12)0.0744 (13)0.0680 (12)0.0229 (11)0.0194 (10)0.0058 (11)
C150.0814 (14)0.0926 (16)0.0873 (14)0.0274 (12)0.0205 (12)0.0149 (13)
C160.0798 (15)0.141 (2)0.0694 (14)0.0328 (16)0.0276 (12)0.0111 (16)
C170.0818 (15)0.116 (2)0.0861 (15)0.0259 (14)0.0406 (12)0.0078 (14)
C180.0764 (13)0.0877 (14)0.0843 (13)0.0220 (11)0.0406 (11)0.0084 (12)
C190.0587 (11)0.0683 (13)0.0676 (11)0.0202 (10)0.0226 (9)0.0090 (10)
C200.0871 (14)0.0701 (13)0.0715 (12)0.0189 (12)0.0393 (11)0.0172 (10)
Geometric parameters (Å, º) top
F—C31.367 (2)C10—C191.507 (2)
N1—C91.343 (2)C10—C111.540 (2)
N1—H1A0.8600C10—H100.9800
N1—H1B0.8600C11—C121.518 (2)
N2—C201.145 (2)C11—H110.9800
C1—C61.381 (2)C12—C131.528 (2)
C1—C21.387 (2)C12—H12A0.9700
C1—H10.9300C12—H12B0.9700
C2—C31.356 (3)C13—C141.505 (2)
C2—H20.9300C13—H13A0.9700
C3—C41.346 (3)C13—H13B0.9700
C4—C51.390 (2)C14—C191.383 (2)
C4—H40.9300C14—C151.396 (2)
C5—C61.379 (2)C15—C161.376 (3)
C5—H50.9300C15—H150.9300
C6—C71.512 (2)C16—C171.365 (3)
C7—C81.515 (2)C16—H160.9300
C7—C111.549 (2)C17—C181.369 (2)
C7—H70.9800C17—H170.9300
C8—C91.349 (2)C18—C191.395 (2)
C8—C201.407 (2)C18—H180.9300
C9—C101.514 (2)
C9—N1—H1A120.0C11—C10—H10107.2
C9—N1—H1B120.0C12—C11—C10109.27 (14)
H1A—N1—H1B120.0C12—C11—C7114.62 (13)
C6—C1—C2121.51 (18)C10—C11—C7102.8 (1)
C6—C1—H1119.2C12—C11—H11110.0
C2—C1—H1119.2C10—C11—H11110.0
C3—C2—C1118.19 (18)C7—C11—H11110.0
C3—C2—H2120.9C11—C12—C13110.80 (14)
C1—C2—H2120.9C11—C12—H12A109.5
C4—C3—C2122.89 (18)C13—C12—H12A109.5
C4—C3—F118.9 (2)C11—C12—H12B109.5
C2—C3—F118.2 (2)C13—C12—H12B109.5
C3—C4—C5118.34 (19)H12A—C12—H12B108.1
C3—C4—H4120.8C14—C13—C12113.53 (15)
C5—C4—H4120.8C14—C13—H13A108.9
C6—C5—C4121.49 (18)C12—C13—H13A108.9
C6—C5—H5119.3C14—C13—H13B108.9
C4—C5—H5119.3C12—C13—H13B108.9
C5—C6—C1117.56 (16)H13A—C13—H13B107.7
C5—C6—C7122.61 (16)C19—C14—C15118.59 (19)
C1—C6—C7119.83 (16)C19—C14—C13120.78 (16)
C6—C7—C8116.5 (1)C15—C14—C13120.6 (2)
C6—C7—C11116.79 (14)C16—C15—C14120.9 (2)
C8—C7—C11101.0 (1)C16—C15—H15119.6
C6—C7—H7107.3C14—C15—H15119.6
C8—C7—H7107.3C17—C16—C15120.6 (2)
C11—C7—H7107.3C17—C16—H16119.7
C9—C8—C20123.62 (15)C15—C16—H16119.7
C9—C8—C7111.1 (1)C16—C17—C18119.0 (2)
C20—C8—C7124.7 (1)C16—C17—H17120.5
N1—C9—C8128.6 (2)C18—C17—H17120.5
N1—C9—C10121.3 (1)C17—C18—C19121.8 (2)
C8—C9—C10110.0 (1)C17—C18—H18119.1
C19—C10—C9116.33 (14)C19—C18—H18119.1
C19—C10—C11116.57 (14)C14—C19—C18119.09 (17)
C9—C10—C11101.8 (1)C14—C19—C10121.28 (16)
C19—C10—H10107.2C18—C19—C10119.62 (17)
C9—C10—H10107.2N2—C20—C8178.9 (2)
C6—C1—C2—C31.0 (3)C9—C10—C11—C1287.82 (15)
C1—C2—C3—C40.0 (3)C19—C10—C11—C7161.99 (14)
C1—C2—C3—F178.46 (16)C9—C10—C11—C734.32 (16)
C2—C3—C4—C50.8 (3)C6—C7—C11—C1242.9 (2)
F—C3—C4—C5177.64 (16)C8—C7—C11—C1284.48 (16)
C3—C4—C5—C60.7 (3)C6—C7—C11—C10161.37 (14)
C4—C5—C6—C10.3 (3)C8—C7—C11—C1033.98 (16)
C4—C5—C6—C7179.68 (16)C10—C11—C12—C1359.07 (17)
C2—C1—C6—C51.1 (3)C7—C11—C12—C13173.82 (14)
C2—C1—C6—C7178.85 (16)C11—C12—C13—C1451.5 (2)
C5—C6—C7—C835.8 (2)C12—C13—C14—C1923.0 (2)
C1—C6—C7—C8144.18 (15)C12—C13—C14—C15160.10 (16)
C5—C6—C7—C1183.6 (2)C19—C14—C15—C160.3 (3)
C1—C6—C7—C1196.44 (19)C13—C14—C15—C16177.31 (17)
C6—C7—C8—C9149.35 (16)C14—C15—C16—C170.8 (3)
C11—C7—C8—C921.76 (19)C15—C16—C17—C180.3 (3)
C6—C7—C8—C2039.0 (2)C16—C17—C18—C191.9 (3)
C11—C7—C8—C20166.62 (17)C15—C14—C19—C181.2 (3)
C20—C8—C9—N14.6 (3)C13—C14—C19—C18175.78 (15)
C7—C8—C9—N1176.29 (17)C15—C14—C19—C10179.77 (15)
C20—C8—C9—C10171.6 (2)C13—C14—C19—C103.2 (3)
C7—C8—C9—C100.1 (2)C17—C18—C19—C142.3 (3)
N1—C9—C10—C1933.5 (2)C17—C18—C19—C10178.62 (16)
C8—C9—C10—C19150.00 (16)C9—C10—C19—C14107.93 (19)
N1—C9—C10—C11161.3 (2)C11—C10—C19—C1412.2 (2)
C8—C9—C10—C1122.17 (19)C9—C10—C19—C1873.1 (2)
C19—C10—C11—C1239.85 (19)C11—C10—C19—C18166.77 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···N2i0.862.193.019 (2)163
Symmetry code: (i) x+1, y, z+1.
 

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