5-Fluoro-3-(1H-indol-3-ylmeth­yl)-1H-indole

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.

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

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Computing details

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

Crystal data

C17H13FN2	Dx = 1.399 Mg m^−3
Mr = 264.29	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 4629 reflections
a = 6.0723 (3) Å	θ = 2.7–27.4°
b = 7.8662 (3) Å	µ = 0.09 mm^−1
c = 26.2693 (11) Å	T = 296 K
V = 1254.78 (9) Å^3	Block, colourless
Z = 4	0.12 × 0.1 × 0.1 mm
F(000) = 552

Data collection

Bruker APEXII CCD diffractometer	2528 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.063
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θmax = 27.5°, θmin = 2.7°
Tmin = 0.691, Tmax = 0.746	h = −7→7
12005 measured reflections	k = −9→10
2866 independent reflections	l = −34→29

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.047	w = 1/[σ^2(Fo^2) + (0.051P)^2 + 0.4902P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.125	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.53 e Å^−3
2866 reflections	Δρmin = −0.30 e Å^−3
181 parameters	Absolute structure: Flack x determined using 921 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: −0.1 (7)
Primary atom site location: dual

Special details

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 U_iso(H) = 1.2Ueq (C), U_iso(H) = 1.2Ueq (N).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F1	0.0864 (4)	−0.1701 (2)	0.06215 (8)	0.0567 (6)
N1	−0.0566 (4)	0.2923 (3)	0.23358 (10)	0.0325 (6)
H1	−0.163457	0.235536	0.246712	0.039*
N2	0.7008 (4)	0.3284 (3)	0.05286 (9)	0.0366 (6)
H2	0.829218	0.336765	0.039262	0.044*
C6	0.1230 (5)	0.3505 (3)	0.25954 (11)	0.0268 (6)
C5	0.2620 (5)	0.4322 (3)	0.22362 (10)	0.0240 (6)
C8	0.1535 (5)	0.4238 (3)	0.17516 (10)	0.0255 (6)
C14	0.2106 (5)	0.1028 (3)	0.08297 (10)	0.0289 (6)
H14	0.081609	0.123845	0.100979	0.035*
C13	0.3747 (5)	0.2253 (3)	0.07888 (10)	0.0264 (6)
C10	0.3965 (5)	0.3978 (3)	0.09673 (10)	0.0264 (6)
C9	0.2277 (5)	0.4995 (3)	0.12576 (11)	0.0285 (6)
H9A	0.288541	0.611254	0.132574	0.034*
H9B	0.099716	0.514911	0.104165	0.034*
C4	0.4575 (5)	0.5076 (4)	0.24071 (11)	0.0293 (6)
H4	0.552343	0.561101	0.217991	0.035*
C12	0.5690 (5)	0.1875 (4)	0.05142 (10)	0.0316 (6)
C17	0.6017 (6)	0.0300 (4)	0.02794 (11)	0.0394 (8)
H17	0.730172	0.006624	0.009970	0.047*
C7	−0.0405 (5)	0.3383 (4)	0.18325 (11)	0.0312 (6)
H7	−0.145343	0.315036	0.158400	0.037*
C3	0.5069 (6)	0.5007 (4)	0.29232 (12)	0.0371 (7)
H3	0.636564	0.549724	0.304113	0.045*
C11	0.5953 (5)	0.4543 (4)	0.07946 (11)	0.0334 (7)
H11	0.651263	0.562800	0.084954	0.040*
C15	0.2462 (6)	−0.0498 (4)	0.05952 (11)	0.0345 (7)
C1	0.1734 (6)	0.3440 (4)	0.31123 (11)	0.0344 (7)
H1A	0.081012	0.289653	0.334300	0.041*
C16	0.4374 (7)	−0.0887 (4)	0.03240 (12)	0.0419 (8)
H16	0.453295	−0.195077	0.017363	0.050*
C2	0.3651 (6)	0.4213 (4)	0.32682 (12)	0.0374 (7)
H2A	0.401270	0.420605	0.361224	0.045*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0776 (17)	0.0382 (10)	0.0542 (13)	−0.0067 (11)	−0.0121 (12)	−0.0048 (9)
N1	0.0292 (14)	0.0317 (12)	0.0366 (13)	−0.0075 (10)	0.0077 (11)	0.0018 (11)
N2	0.0284 (13)	0.0539 (16)	0.0276 (12)	0.0014 (12)	0.0064 (11)	0.0075 (11)
C6	0.0278 (15)	0.0242 (12)	0.0285 (13)	−0.0002 (11)	0.0056 (12)	−0.0006 (11)
C5	0.0270 (14)	0.0189 (11)	0.0262 (13)	0.0034 (10)	0.0038 (11)	−0.0006 (10)
C8	0.0283 (14)	0.0229 (12)	0.0253 (13)	0.0017 (11)	0.0028 (11)	−0.0011 (10)
C14	0.0341 (16)	0.0307 (14)	0.0220 (13)	0.0051 (12)	−0.0021 (12)	0.0010 (10)
C13	0.0307 (15)	0.0314 (13)	0.0171 (11)	0.0064 (11)	−0.0015 (11)	0.0028 (10)
C10	0.0286 (15)	0.0310 (13)	0.0196 (12)	0.0003 (11)	−0.0006 (11)	0.0040 (10)
C9	0.0337 (15)	0.0263 (12)	0.0256 (13)	0.0023 (12)	−0.0015 (12)	0.0007 (11)
C4	0.0296 (15)	0.0283 (13)	0.0299 (14)	−0.0019 (12)	0.0038 (12)	−0.0016 (11)
C12	0.0325 (16)	0.0433 (16)	0.0191 (12)	0.0083 (13)	0.0004 (12)	0.0052 (11)
C17	0.0423 (19)	0.0527 (19)	0.0233 (14)	0.0218 (16)	0.0028 (14)	0.0028 (13)
C7	0.0293 (15)	0.0312 (14)	0.0329 (15)	−0.0005 (12)	−0.0013 (12)	−0.0012 (12)
C3	0.0363 (18)	0.0389 (16)	0.0361 (16)	−0.0004 (14)	−0.0076 (14)	−0.0065 (13)
C11	0.0344 (17)	0.0390 (16)	0.0268 (14)	−0.0031 (13)	−0.0008 (13)	0.0070 (12)
C15	0.0465 (19)	0.0304 (14)	0.0265 (14)	0.0038 (13)	−0.0086 (14)	0.0013 (11)
C1	0.0425 (18)	0.0313 (14)	0.0294 (15)	0.0008 (13)	0.0117 (13)	0.0009 (12)
C16	0.063 (2)	0.0365 (16)	0.0256 (14)	0.0183 (16)	−0.0052 (16)	−0.0024 (12)
C2	0.0442 (19)	0.0417 (16)	0.0262 (14)	0.0063 (15)	−0.0012 (14)	−0.0030 (13)

Geometric parameters (Å, º)

F1—C15	1.357 (4)	C10—C9	1.507 (4)
N1—H1	0.8600	C10—C11	1.364 (4)
N1—C6	1.365 (4)	C9—H9A	0.9700
N1—C7	1.374 (4)	C9—H9B	0.9700
N2—H2	0.8600	C4—H4	0.9300
N2—C12	1.368 (4)	C4—C3	1.390 (4)
N2—C11	1.371 (4)	C12—C17	1.398 (4)
C6—C5	1.420 (4)	C17—H17	0.9300
C6—C1	1.393 (4)	C17—C16	1.372 (5)
C5—C8	1.435 (4)	C7—H7	0.9300
C5—C4	1.401 (4)	C3—H3	0.9300
C8—C9	1.497 (4)	C3—C2	1.398 (5)
C8—C7	1.373 (4)	C11—H11	0.9300
C14—H14	0.9300	C15—C16	1.396 (5)
C14—C13	1.391 (4)	C1—H1A	0.9300
C14—C15	1.366 (4)	C1—C2	1.375 (5)
C13—C10	1.442 (4)	C16—H16	0.9300
C13—C12	1.415 (4)	C2—H2A	0.9300
C6—N1—H1	125.2	C5—C4—H4	120.7
C6—N1—C7	109.6 (2)	C3—C4—C5	118.6 (3)
C7—N1—H1	125.2	C3—C4—H4	120.7
C12—N2—H2	125.5	N2—C12—C13	107.7 (3)
C12—N2—C11	109.0 (3)	N2—C12—C17	130.3 (3)
C11—N2—H2	125.5	C17—C12—C13	122.0 (3)
N1—C6—C5	107.1 (2)	C12—C17—H17	121.2
N1—C6—C1	130.6 (3)	C16—C17—C12	117.5 (3)
C1—C6—C5	122.3 (3)	C16—C17—H17	121.2
C6—C5—C8	107.2 (2)	N1—C7—H7	125.1
C4—C5—C6	118.8 (2)	C8—C7—N1	109.8 (3)
C4—C5—C8	133.9 (3)	C8—C7—H7	125.1
C5—C8—C9	127.7 (3)	C4—C3—H3	119.4
C7—C8—C5	106.2 (2)	C4—C3—C2	121.2 (3)
C7—C8—C9	126.0 (3)	C2—C3—H3	119.4
C13—C14—H14	121.3	N2—C11—H11	124.8
C15—C14—H14	121.3	C10—C11—N2	110.4 (3)
C15—C14—C13	117.4 (3)	C10—C11—H11	124.8
C14—C13—C10	133.9 (3)	F1—C15—C14	118.4 (3)
C14—C13—C12	119.4 (3)	F1—C15—C16	117.9 (3)
C12—C13—C10	106.7 (3)	C14—C15—C16	123.7 (3)
C13—C10—C9	127.0 (3)	C6—C1—H1A	121.3
C11—C10—C13	106.2 (3)	C2—C1—C6	117.4 (3)
C11—C10—C9	126.7 (3)	C2—C1—H1A	121.3
C8—C9—C10	115.6 (2)	C17—C16—C15	119.9 (3)
C8—C9—H9A	108.4	C17—C16—H16	120.0
C8—C9—H9B	108.4	C15—C16—H16	120.0
C10—C9—H9A	108.4	C3—C2—H2A	119.1
C10—C9—H9B	108.4	C1—C2—C3	121.7 (3)
H9A—C9—H9B	107.4	C1—C2—H2A	119.1
F1—C15—C16—C17	178.8 (3)	C13—C10—C11—N2	−1.1 (3)
N1—C6—C5—C8	1.5 (3)	C13—C12—C17—C16	0.0 (4)
N1—C6—C5—C4	178.5 (2)	C10—C13—C12—N2	0.3 (3)
N1—C6—C1—C2	−177.1 (3)	C10—C13—C12—C17	−179.0 (3)
N2—C12—C17—C16	−179.2 (3)	C9—C8—C7—N1	−177.8 (3)
C6—N1—C7—C8	1.6 (3)	C9—C10—C11—N2	−177.5 (3)
C6—C5—C8—C9	176.6 (3)	C4—C5—C8—C9	0.2 (5)
C6—C5—C8—C7	−0.5 (3)	C4—C5—C8—C7	−176.9 (3)
C6—C5—C4—C3	−0.6 (4)	C4—C3—C2—C1	1.2 (5)
C6—C1—C2—C3	−1.2 (5)	C12—N2—C11—C10	1.3 (3)
C5—C6—C1—C2	0.2 (4)	C12—C13—C10—C9	176.9 (3)
C5—C8—C9—C10	81.7 (4)	C12—C13—C10—C11	0.4 (3)
C5—C8—C7—N1	−0.6 (3)	C12—C17—C16—C15	0.1 (4)
C5—C4—C3—C2	−0.3 (5)	C7—N1—C6—C5	−1.9 (3)
C8—C5—C4—C3	175.5 (3)	C7—N1—C6—C1	175.8 (3)
C14—C13—C10—C9	−2.1 (5)	C7—C8—C9—C10	−101.7 (3)
C14—C13—C10—C11	−178.6 (3)	C11—N2—C12—C13	−1.0 (3)
C14—C13—C12—N2	179.5 (2)	C11—N2—C12—C17	178.3 (3)
C14—C13—C12—C17	0.2 (4)	C11—C10—C9—C8	−126.1 (3)
C14—C15—C16—C17	−0.4 (5)	C15—C14—C13—C10	178.5 (3)
C13—C14—C15—F1	−178.7 (2)	C15—C14—C13—C12	−0.4 (4)
C13—C14—C15—C16	0.6 (4)	C1—C6—C5—C8	−176.4 (3)
C13—C10—C9—C8	58.2 (4)	C1—C6—C5—C4	0.6 (4)