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The title compound, C17H13FN2, was synthesized as a potential ligand for the construction of metal–organic frameworks. The two indole motifs present two potential coordination modes. It crystallizes in the ortho­rhom­bic system with space group P212121. The dihedral angle between the fused ring systems is 68.77 (10)°. Weak F...H inter­actions are observed in the crystal.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314623005904/xu4049sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314623005904/xu4049Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314623005904/xu4049Isup3.cml
Supplementary material

CCDC reference: 2233347

Key indicators

Structure: I
  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.047
  • wR factor = 0.125
  • Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level C STRVA01_ALERT_4_C Flack test results are meaningless. From the CIF: _refine_ls_abs_structure_Flack -0.100 From the CIF: _refine_ls_abs_structure_Flack_su 0.700 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00417 Ang. PLAT420_ALERT_2_C D-H Bond Without Acceptor N1 --H1 . Please Check PLAT420_ALERT_2_C D-H Bond Without Acceptor N2 --H2 . Please Check PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 4 Report
Alert level G PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 2 Report PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High . 0.700 Report PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF .... 3 Note PLAT916_ALERT_2_G Hooft y and Flack x Parameter Values Differ by . 0.20 Check PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 4 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 5 ALERT level C = Check. Ensure it is not caused by an omission or oversight 6 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Computing details top

Data collection: Bruker APEXII CCD; cell refinement: SAINT V8.40A (Bruker, 2019); data reduction: SAINT V8.40A (Bruker, 2019); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: Olex2 1.3 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 1.3 (Dolomanov et al., 2009).

5-Fluoro-3-(1H-indol-3-ylmethyl)-1H-indole top
Crystal data top
C17H13FN2Dx = 1.399 Mg m3
Mr = 264.29Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 4629 reflections
a = 6.0723 (3) Åθ = 2.7–27.4°
b = 7.8662 (3) ŵ = 0.09 mm1
c = 26.2693 (11) ÅT = 296 K
V = 1254.78 (9) Å3Block, colourless
Z = 40.12 × 0.1 × 0.1 mm
F(000) = 552
Data collection top
Bruker APEXII CCD
diffractometer
2528 reflections with I > 2σ(I)
φ and ω scansRint = 0.063
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
θmax = 27.5°, θmin = 2.7°
Tmin = 0.691, Tmax = 0.746h = 77
12005 measured reflectionsk = 910
2866 independent reflectionsl = 3429
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.047 w = 1/[σ2(Fo2) + (0.051P)2 + 0.4902P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.125(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.53 e Å3
2866 reflectionsΔρmin = 0.30 e Å3
181 parametersAbsolute structure: Flack x determined using 921 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraintsAbsolute structure parameter: 0.1 (7)
Primary atom site location: dual
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The H atoms were included in calculated positions and treated as riding atoms: C–H = 0.93- 0.98 Å, with Uiso(H) = 1.2Ueq (C), Uiso(H) = 1.2Ueq (N).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.0864 (4)0.1701 (2)0.06215 (8)0.0567 (6)
N10.0566 (4)0.2923 (3)0.23358 (10)0.0325 (6)
H10.1634570.2355360.2467120.039*
N20.7008 (4)0.3284 (3)0.05286 (9)0.0366 (6)
H20.8292180.3367650.0392620.044*
C60.1230 (5)0.3505 (3)0.25954 (11)0.0268 (6)
C50.2620 (5)0.4322 (3)0.22362 (10)0.0240 (6)
C80.1535 (5)0.4238 (3)0.17516 (10)0.0255 (6)
C140.2106 (5)0.1028 (3)0.08297 (10)0.0289 (6)
H140.0816090.1238450.1009790.035*
C130.3747 (5)0.2253 (3)0.07888 (10)0.0264 (6)
C100.3965 (5)0.3978 (3)0.09673 (10)0.0264 (6)
C90.2277 (5)0.4995 (3)0.12576 (11)0.0285 (6)
H9A0.2885410.6112540.1325740.034*
H9B0.0997160.5149110.1041650.034*
C40.4575 (5)0.5076 (4)0.24071 (11)0.0293 (6)
H40.5523430.5611010.2179910.035*
C120.5690 (5)0.1875 (4)0.05142 (10)0.0316 (6)
C170.6017 (6)0.0300 (4)0.02794 (11)0.0394 (8)
H170.7301720.0066240.0099700.047*
C70.0405 (5)0.3383 (4)0.18325 (11)0.0312 (6)
H70.1453430.3150360.1584000.037*
C30.5069 (6)0.5007 (4)0.29232 (12)0.0371 (7)
H30.6365640.5497240.3041130.045*
C110.5953 (5)0.4543 (4)0.07946 (11)0.0334 (7)
H110.6512630.5628000.0849540.040*
C150.2462 (6)0.0498 (4)0.05952 (11)0.0345 (7)
C10.1734 (6)0.3440 (4)0.31123 (11)0.0344 (7)
H1A0.0810120.2896530.3343000.041*
C160.4374 (7)0.0887 (4)0.03240 (12)0.0419 (8)
H160.4532950.1950770.0173630.050*
C20.3651 (6)0.4213 (4)0.32682 (12)0.0374 (7)
H2A0.4012700.4206050.3612240.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0776 (17)0.0382 (10)0.0542 (13)0.0067 (11)0.0121 (12)0.0048 (9)
N10.0292 (14)0.0317 (12)0.0366 (13)0.0075 (10)0.0077 (11)0.0018 (11)
N20.0284 (13)0.0539 (16)0.0276 (12)0.0014 (12)0.0064 (11)0.0075 (11)
C60.0278 (15)0.0242 (12)0.0285 (13)0.0002 (11)0.0056 (12)0.0006 (11)
C50.0270 (14)0.0189 (11)0.0262 (13)0.0034 (10)0.0038 (11)0.0006 (10)
C80.0283 (14)0.0229 (12)0.0253 (13)0.0017 (11)0.0028 (11)0.0011 (10)
C140.0341 (16)0.0307 (14)0.0220 (13)0.0051 (12)0.0021 (12)0.0010 (10)
C130.0307 (15)0.0314 (13)0.0171 (11)0.0064 (11)0.0015 (11)0.0028 (10)
C100.0286 (15)0.0310 (13)0.0196 (12)0.0003 (11)0.0006 (11)0.0040 (10)
C90.0337 (15)0.0263 (12)0.0256 (13)0.0023 (12)0.0015 (12)0.0007 (11)
C40.0296 (15)0.0283 (13)0.0299 (14)0.0019 (12)0.0038 (12)0.0016 (11)
C120.0325 (16)0.0433 (16)0.0191 (12)0.0083 (13)0.0004 (12)0.0052 (11)
C170.0423 (19)0.0527 (19)0.0233 (14)0.0218 (16)0.0028 (14)0.0028 (13)
C70.0293 (15)0.0312 (14)0.0329 (15)0.0005 (12)0.0013 (12)0.0012 (12)
C30.0363 (18)0.0389 (16)0.0361 (16)0.0004 (14)0.0076 (14)0.0065 (13)
C110.0344 (17)0.0390 (16)0.0268 (14)0.0031 (13)0.0008 (13)0.0070 (12)
C150.0465 (19)0.0304 (14)0.0265 (14)0.0038 (13)0.0086 (14)0.0013 (11)
C10.0425 (18)0.0313 (14)0.0294 (15)0.0008 (13)0.0117 (13)0.0009 (12)
C160.063 (2)0.0365 (16)0.0256 (14)0.0183 (16)0.0052 (16)0.0024 (12)
C20.0442 (19)0.0417 (16)0.0262 (14)0.0063 (15)0.0012 (14)0.0030 (13)
Geometric parameters (Å, º) top
F1—C151.357 (4)C10—C91.507 (4)
N1—H10.8600C10—C111.364 (4)
N1—C61.365 (4)C9—H9A0.9700
N1—C71.374 (4)C9—H9B0.9700
N2—H20.8600C4—H40.9300
N2—C121.368 (4)C4—C31.390 (4)
N2—C111.371 (4)C12—C171.398 (4)
C6—C51.420 (4)C17—H170.9300
C6—C11.393 (4)C17—C161.372 (5)
C5—C81.435 (4)C7—H70.9300
C5—C41.401 (4)C3—H30.9300
C8—C91.497 (4)C3—C21.398 (5)
C8—C71.373 (4)C11—H110.9300
C14—H140.9300C15—C161.396 (5)
C14—C131.391 (4)C1—H1A0.9300
C14—C151.366 (4)C1—C21.375 (5)
C13—C101.442 (4)C16—H160.9300
C13—C121.415 (4)C2—H2A0.9300
C6—N1—H1125.2C5—C4—H4120.7
C6—N1—C7109.6 (2)C3—C4—C5118.6 (3)
C7—N1—H1125.2C3—C4—H4120.7
C12—N2—H2125.5N2—C12—C13107.7 (3)
C12—N2—C11109.0 (3)N2—C12—C17130.3 (3)
C11—N2—H2125.5C17—C12—C13122.0 (3)
N1—C6—C5107.1 (2)C12—C17—H17121.2
N1—C6—C1130.6 (3)C16—C17—C12117.5 (3)
C1—C6—C5122.3 (3)C16—C17—H17121.2
C6—C5—C8107.2 (2)N1—C7—H7125.1
C4—C5—C6118.8 (2)C8—C7—N1109.8 (3)
C4—C5—C8133.9 (3)C8—C7—H7125.1
C5—C8—C9127.7 (3)C4—C3—H3119.4
C7—C8—C5106.2 (2)C4—C3—C2121.2 (3)
C7—C8—C9126.0 (3)C2—C3—H3119.4
C13—C14—H14121.3N2—C11—H11124.8
C15—C14—H14121.3C10—C11—N2110.4 (3)
C15—C14—C13117.4 (3)C10—C11—H11124.8
C14—C13—C10133.9 (3)F1—C15—C14118.4 (3)
C14—C13—C12119.4 (3)F1—C15—C16117.9 (3)
C12—C13—C10106.7 (3)C14—C15—C16123.7 (3)
C13—C10—C9127.0 (3)C6—C1—H1A121.3
C11—C10—C13106.2 (3)C2—C1—C6117.4 (3)
C11—C10—C9126.7 (3)C2—C1—H1A121.3
C8—C9—C10115.6 (2)C17—C16—C15119.9 (3)
C8—C9—H9A108.4C17—C16—H16120.0
C8—C9—H9B108.4C15—C16—H16120.0
C10—C9—H9A108.4C3—C2—H2A119.1
C10—C9—H9B108.4C1—C2—C3121.7 (3)
H9A—C9—H9B107.4C1—C2—H2A119.1
F1—C15—C16—C17178.8 (3)C13—C10—C11—N21.1 (3)
N1—C6—C5—C81.5 (3)C13—C12—C17—C160.0 (4)
N1—C6—C5—C4178.5 (2)C10—C13—C12—N20.3 (3)
N1—C6—C1—C2177.1 (3)C10—C13—C12—C17179.0 (3)
N2—C12—C17—C16179.2 (3)C9—C8—C7—N1177.8 (3)
C6—N1—C7—C81.6 (3)C9—C10—C11—N2177.5 (3)
C6—C5—C8—C9176.6 (3)C4—C5—C8—C90.2 (5)
C6—C5—C8—C70.5 (3)C4—C5—C8—C7176.9 (3)
C6—C5—C4—C30.6 (4)C4—C3—C2—C11.2 (5)
C6—C1—C2—C31.2 (5)C12—N2—C11—C101.3 (3)
C5—C6—C1—C20.2 (4)C12—C13—C10—C9176.9 (3)
C5—C8—C9—C1081.7 (4)C12—C13—C10—C110.4 (3)
C5—C8—C7—N10.6 (3)C12—C17—C16—C150.1 (4)
C5—C4—C3—C20.3 (5)C7—N1—C6—C51.9 (3)
C8—C5—C4—C3175.5 (3)C7—N1—C6—C1175.8 (3)
C14—C13—C10—C92.1 (5)C7—C8—C9—C10101.7 (3)
C14—C13—C10—C11178.6 (3)C11—N2—C12—C131.0 (3)
C14—C13—C12—N2179.5 (2)C11—N2—C12—C17178.3 (3)
C14—C13—C12—C170.2 (4)C11—C10—C9—C8126.1 (3)
C14—C15—C16—C170.4 (5)C15—C14—C13—C10178.5 (3)
C13—C14—C15—F1178.7 (2)C15—C14—C13—C120.4 (4)
C13—C14—C15—C160.6 (4)C1—C6—C5—C8176.4 (3)
C13—C10—C9—C858.2 (4)C1—C6—C5—C40.6 (4)
Intermolecular interactions (Å) top
Atom1Atom2Symm. op. 2LengthLength - vdW
F1H16-1/2 + x, -1/2 - y, -z2.48-0.19
C1H41 - x, -1/2 + y, 1/2 - z2.88-0.02
C4H1-x, 1/2 + y, 1/2 - z2.55-0.35
C5H1-x, 1/2 + y, 1/2 - z2.58-0.32
C11H71 + x, y, z2.82-0.08
C12H2-1/2 + x, 1/2 - y, -z2.80-0.10
C16H2-1/2 + x, 1/2 - y, -z2.81-0.09
C17H2-1/2 + x, 1/2 - y, -z2.64-0.26
 

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