5-Benzyl-1-(4-fluoro­phen­yl)-2-phenyl-4,5,6,7-tetra­hydro-1H-pyrrolo[3,2-c]pyridine

In the title compound, C₂₆H₂₃FN₂, the dihedral angle between the 4-fluoro­phenyl ring and the adjacent phenyl ring is 62.3 (1)°. The crystal structure is stabilized by C—H...π interactions.

Key indicators

• Single-crystal X-ray study
• T = 290 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.082
• wR factor = 0.137
• Data-to-parameter ratio = 11.2

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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, 1999) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).

1-(4-fluorophenyl)-5-benzyl-2-phenyl-4,5,6,7-tetrahydro-1H-pyrrolo [3,2-c]pyridine

Crystal data

C26H23FN2	F(000) = 808
Mr = 382.46	Dx = 1.264 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 650 reflections
a = 13.220 (8) Å	θ = 1.4–25.8°
b = 18.431 (11) Å	µ = 0.08 mm^−1
c = 8.475 (5) Å	T = 290 K
β = 103.223 (11)°	Block, colourless
V = 2010 (2) Å^3	0.25 × 0.20 × 0.15 mm
Z = 4

Data collection

Bruker SMART APEX CCD area detector diffractometer	3975 independent reflections
Radiation source: fine-focus sealed tube	2935 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ and ω scans	θmax = 26.4°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
Tmin = 0.939, Tmax = 0.988	k = −22→22
15238 measured reflections	l = −10→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.082	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.137	All H-atom parameters refined
S = 1.23	w = 1/[σ^2(Fo^2) + (0.0366P)^2 + 0.563P] where P = (Fo^2 + 2Fc^2)/3
3975 reflections	(Δ/σ)max < 0.001
354 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	−0.16351 (15)	0.12112 (11)	0.2533 (2)	0.0450 (5)
N2	0.10267 (14)	0.08638 (11)	0.0874 (2)	0.0430 (5)
F1	0.45373 (16)	−0.06628 (13)	0.3790 (2)	0.1136 (8)
C1	0.08574 (18)	0.12983 (13)	−0.0506 (3)	0.0423 (6)
C2	−0.0044 (2)	0.16729 (14)	−0.0555 (3)	0.0459 (6)
C3	−0.04389 (17)	0.14767 (13)	0.0801 (3)	0.0420 (6)
C4	0.02284 (17)	0.09843 (13)	0.1666 (3)	0.0427 (6)
C5	−0.1404 (2)	0.17053 (14)	0.1305 (3)	0.0453 (6)
C6	−0.0704 (2)	0.10760 (18)	0.3831 (3)	0.0536 (7)
C7	0.0110 (2)	0.06458 (16)	0.3211 (3)	0.0507 (7)
C8	0.19487 (18)	0.04667 (13)	0.1585 (3)	0.0424 (6)
C9	0.1868 (2)	−0.02574 (16)	0.1964 (3)	0.0547 (7)
C10	0.2748 (3)	−0.06376 (19)	0.2709 (4)	0.0671 (9)
C11	0.3676 (3)	−0.0290 (2)	0.3046 (3)	0.0702 (10)
C12	0.3782 (2)	0.0417 (2)	0.2657 (4)	0.0667 (9)
C13	0.2903 (2)	0.08005 (17)	0.1930 (3)	0.0517 (7)
C14	0.15117 (18)	0.13009 (13)	−0.1704 (3)	0.0431 (6)
C15	0.1580 (2)	0.19339 (16)	−0.2582 (3)	0.0504 (7)
C16	0.2159 (2)	0.19506 (18)	−0.3747 (3)	0.0588 (8)
C17	0.2689 (2)	0.13476 (19)	−0.4063 (4)	0.0612 (8)
C18	0.2626 (2)	0.07170 (18)	−0.3223 (4)	0.0572 (7)
C19	0.2037 (2)	0.06874 (15)	−0.2061 (3)	0.0481 (7)
C20	−0.2464 (2)	0.14983 (19)	0.3236 (4)	0.0568 (7)
C21	−0.3899 (2)	0.10992 (18)	0.0904 (4)	0.0573 (8)
C22	−0.4849 (2)	0.1204 (2)	−0.0142 (4)	0.0701 (9)
C23	−0.5394 (3)	0.1824 (2)	−0.0056 (5)	0.0758 (10)
C24	−0.4994 (3)	0.2345 (2)	0.1052 (5)	0.0855 (11)
C25	−0.4043 (2)	0.22419 (19)	0.2103 (4)	0.0691 (9)
C26	−0.34823 (19)	0.16168 (15)	0.2048 (3)	0.0487 (7)
H2	−0.0347 (16)	0.1976 (12)	−0.140 (3)	0.038 (6)*
H5B	−0.1348 (17)	0.2206 (14)	0.171 (3)	0.048 (7)*
H5A	−0.2027 (18)	0.1689 (12)	0.033 (3)	0.042 (6)*
H6A	−0.0933 (19)	0.0799 (14)	0.469 (3)	0.059 (8)*
H6B	−0.041 (2)	0.1552 (15)	0.432 (3)	0.062 (8)*
H7A	−0.0110 (19)	0.0125 (15)	0.305 (3)	0.056 (8)*
H7B	0.0736 (19)	0.0663 (12)	0.402 (3)	0.047 (7)*
H9	0.120 (2)	−0.0480 (14)	0.171 (3)	0.063 (9)*
H10	0.269 (2)	−0.1116 (16)	0.296 (3)	0.065 (9)*
H11	0.1235 (18)	0.2338 (13)	−0.235 (3)	0.044 (7)*
H12	0.442 (2)	0.0668 (15)	0.290 (4)	0.075 (10)*
H13	0.2968 (18)	0.1277 (14)	0.169 (3)	0.045 (7)*
H16	0.217 (2)	0.2383 (15)	−0.432 (3)	0.063 (8)*
H17	0.309 (2)	0.1363 (15)	−0.484 (3)	0.067 (9)*
H18	0.298 (2)	0.0278 (15)	−0.348 (3)	0.068 (9)*
H19	0.1984 (18)	0.0231 (14)	−0.155 (3)	0.048 (7)*
H21	−0.352 (2)	0.0672 (15)	0.079 (3)	0.065 (9)*
H22	−0.511 (2)	0.0843 (17)	−0.090 (4)	0.080 (10)*
H23	−0.604 (2)	0.1888 (16)	−0.077 (4)	0.077 (9)*
H24	−0.532 (3)	0.2779 (19)	0.113 (4)	0.097 (12)*
H24B	−0.2271 (18)	0.1966 (14)	0.383 (3)	0.054 (7)*
H24A	−0.257 (2)	0.1144 (14)	0.406 (3)	0.061 (8)*
H25	−0.374 (2)	0.2590 (16)	0.287 (4)	0.075 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0368 (11)	0.0540 (13)	0.0423 (12)	0.0031 (10)	0.0055 (10)	0.0013 (10)
N2	0.0327 (11)	0.0467 (12)	0.0465 (12)	0.0009 (9)	0.0029 (10)	0.0110 (10)
F1	0.0981 (15)	0.156 (2)	0.0750 (13)	0.0816 (15)	−0.0052 (11)	0.0091 (13)
C1	0.0362 (13)	0.0399 (14)	0.0468 (15)	−0.0042 (11)	0.0015 (12)	0.0081 (12)
C2	0.0418 (15)	0.0433 (14)	0.0479 (16)	0.0005 (12)	0.0005 (12)	0.0128 (13)
C3	0.0333 (13)	0.0413 (14)	0.0471 (15)	−0.0018 (11)	0.0002 (11)	0.0043 (12)
C4	0.0321 (13)	0.0459 (14)	0.0471 (15)	−0.0036 (11)	0.0026 (11)	0.0073 (12)
C5	0.0424 (15)	0.0402 (15)	0.0484 (16)	0.0014 (12)	0.0005 (13)	0.0000 (13)
C6	0.0463 (16)	0.067 (2)	0.0438 (16)	−0.0009 (14)	0.0022 (14)	0.0066 (15)
C7	0.0360 (15)	0.0604 (19)	0.0506 (17)	−0.0002 (13)	−0.0009 (13)	0.0141 (14)
C8	0.0396 (14)	0.0490 (15)	0.0365 (13)	0.0056 (12)	0.0045 (11)	0.0036 (12)
C9	0.0604 (19)	0.0535 (18)	0.0486 (16)	0.0057 (15)	0.0089 (15)	0.0041 (14)
C10	0.094 (3)	0.055 (2)	0.0511 (18)	0.0281 (19)	0.0152 (18)	0.0075 (15)
C11	0.068 (2)	0.097 (3)	0.0412 (17)	0.046 (2)	0.0029 (16)	0.0055 (17)
C12	0.0376 (17)	0.108 (3)	0.0503 (18)	0.0107 (19)	0.0016 (14)	−0.0025 (18)
C13	0.0398 (15)	0.0616 (19)	0.0507 (17)	−0.0021 (14)	0.0044 (13)	0.0025 (15)
C14	0.0362 (13)	0.0462 (15)	0.0409 (14)	−0.0071 (11)	−0.0033 (11)	0.0025 (12)
C15	0.0525 (17)	0.0494 (17)	0.0458 (16)	−0.0026 (14)	0.0042 (13)	0.0024 (13)
C16	0.068 (2)	0.062 (2)	0.0434 (17)	−0.0149 (16)	0.0062 (15)	0.0089 (15)
C17	0.0605 (19)	0.081 (2)	0.0424 (17)	−0.0150 (17)	0.0133 (15)	−0.0097 (16)
C18	0.0525 (17)	0.065 (2)	0.0526 (18)	−0.0029 (15)	0.0089 (14)	−0.0115 (16)
C19	0.0454 (15)	0.0445 (16)	0.0486 (16)	−0.0049 (12)	−0.0013 (13)	0.0002 (13)
C20	0.0530 (18)	0.068 (2)	0.0477 (17)	0.0057 (15)	0.0088 (14)	−0.0053 (16)
C21	0.0503 (18)	0.065 (2)	0.0578 (18)	0.0041 (15)	0.0150 (15)	−0.0061 (15)
C22	0.0476 (19)	0.100 (3)	0.061 (2)	−0.0030 (19)	0.0082 (16)	−0.011 (2)
C23	0.0360 (17)	0.117 (3)	0.073 (2)	0.0057 (19)	0.0086 (17)	0.009 (2)
C24	0.060 (2)	0.088 (3)	0.107 (3)	0.028 (2)	0.015 (2)	−0.004 (2)
C25	0.0530 (19)	0.073 (2)	0.080 (2)	0.0068 (17)	0.0130 (18)	−0.0158 (19)
C26	0.0390 (14)	0.0617 (17)	0.0492 (16)	0.0028 (13)	0.0178 (12)	−0.0027 (13)

Geometric parameters (Å, º)

N2—C4	1.392 (3)	C13—H13	0.91 (2)
N2—C1	1.393 (3)	C15—C16	1.380 (4)
N2—C8	1.431 (3)	C15—H11	0.92 (2)
F1—C11	1.356 (3)	C6—C7	1.524 (4)
N1—C20	1.461 (3)	C6—H6A	0.99 (3)
N1—C5	1.467 (3)	C6—H6B	1.01 (3)
N1—C6	1.473 (3)	C17—C16	1.372 (4)
C4—C3	1.358 (3)	C17—C18	1.375 (4)
C4—C7	1.490 (4)	C17—H17	0.94 (3)
C14—C19	1.396 (4)	C12—C11	1.359 (5)
C14—C15	1.398 (4)	C12—H12	0.94 (3)
C14—C1	1.476 (3)	C7—H7B	0.95 (2)
C3—C2	1.414 (3)	C7—H7A	1.00 (3)
C3—C5	1.495 (4)	C16—H16	0.94 (3)
C8—C13	1.373 (4)	C9—C10	1.382 (4)
C8—C9	1.382 (4)	C9—H9	0.96 (3)
C19—C18	1.389 (4)	C10—C11	1.354 (5)
C19—H19	0.96 (2)	C10—H10	0.91 (3)
C2—C1	1.369 (3)	C24—C23	1.363 (5)
C2—H2	0.92 (2)	C24—C25	1.377 (5)
C5—H5B	0.98 (3)	C24—H24	0.92 (3)
C5—H5A	1.02 (2)	C22—C23	1.361 (5)
C26—C25	1.376 (4)	C22—C21	1.375 (4)
C26—C21	1.382 (4)	C22—H22	0.94 (3)
C26—C20	1.501 (4)	C18—H18	0.98 (3)
C20—H24B	1.00 (3)	C21—H21	0.95 (3)
C20—H24A	0.99 (3)	C25—H25	0.94 (3)
C13—C12	1.379 (4)	C23—H23	0.94 (3)
C4—N2—C1	108.63 (19)	N1—C6—C7	111.5 (2)
C4—N2—C8	123.0 (2)	N1—C6—H6A	106.9 (15)
C1—N2—C8	127.2 (2)	C7—C6—H6A	110.1 (15)
C20—N1—C5	111.2 (2)	N1—C6—H6B	109.9 (15)
C20—N1—C6	109.5 (2)	C7—C6—H6B	110.6 (15)
C5—N1—C6	111.1 (2)	H6A—C6—H6B	108 (2)
C3—C4—N2	108.5 (2)	C16—C17—C18	119.3 (3)
C3—C4—C7	124.6 (2)	C16—C17—H17	120.6 (17)
N2—C4—C7	126.9 (2)	C18—C17—H17	120.0 (17)
C19—C14—C15	117.7 (3)	C11—C12—C13	118.5 (3)
C19—C14—C1	123.0 (2)	C11—C12—H12	123.5 (18)
C15—C14—C1	119.2 (2)	C13—C12—H12	117.9 (19)
C4—C3—C2	107.1 (2)	C4—C7—C6	108.0 (2)
C4—C3—C5	121.7 (2)	C4—C7—H7B	111.9 (14)
C2—C3—C5	131.1 (2)	C6—C7—H7B	107.5 (14)
C13—C8—C9	119.9 (2)	C4—C7—H7A	111.7 (14)
C13—C8—N2	120.9 (2)	C6—C7—H7A	109.7 (14)
C9—C8—N2	119.2 (2)	H7B—C7—H7A	108 (2)
C18—C19—C14	120.6 (3)	C17—C16—C15	120.8 (3)
C18—C19—H19	117.8 (14)	C17—C16—H16	121.2 (17)
C14—C19—H19	121.5 (14)	C15—C16—H16	118.0 (17)
C1—C2—C3	109.1 (2)	C10—C9—C8	119.6 (3)
C1—C2—H2	123.4 (14)	C10—C9—H9	121.8 (16)
C3—C2—H2	127.4 (14)	C8—C9—H9	118.6 (16)
N1—C5—C3	110.9 (2)	C11—C10—C9	118.9 (3)
N1—C5—H5B	110.4 (14)	C11—C10—H10	121.6 (18)
C3—C5—H5B	111.3 (14)	C9—C10—H10	119.5 (18)
N1—C5—H5A	107.1 (12)	C10—C11—F1	118.8 (4)
C3—C5—H5A	110.1 (12)	C10—C11—C12	122.8 (3)
H5B—C5—H5A	106.8 (18)	F1—C11—C12	118.4 (4)
C25—C26—C21	118.0 (3)	C23—C24—C25	120.1 (4)
C25—C26—C20	120.4 (3)	C23—C24—H24	123 (2)
C21—C26—C20	121.5 (3)	C25—C24—H24	117 (2)
N1—C20—C26	114.9 (2)	C23—C22—C21	120.0 (4)
N1—C20—H24B	112.8 (14)	C23—C22—H22	120.8 (19)
C26—C20—H24B	107.3 (14)	C21—C22—H22	119.2 (19)
N1—C20—H24A	107.0 (15)	C17—C18—C19	120.6 (3)
C26—C20—H24A	108.6 (15)	C17—C18—H18	119.8 (16)
H24B—C20—H24A	106 (2)	C19—C18—H18	119.5 (16)
C2—C1—N2	106.6 (2)	C22—C21—C26	120.9 (3)
C2—C1—C14	128.3 (2)	C22—C21—H21	118.7 (17)
N2—C1—C14	124.9 (2)	C26—C21—H21	120.3 (17)
C8—C13—C12	120.3 (3)	C26—C25—C24	120.9 (3)
C8—C13—H13	120.9 (15)	C26—C25—H25	116.5 (18)
C12—C13—H13	118.8 (15)	C24—C25—H25	122.6 (18)
C16—C15—C14	120.9 (3)	C22—C23—C24	120.1 (3)
C16—C15—H11	121.3 (15)	C22—C23—H23	119.2 (19)
C14—C15—H11	117.8 (15)	C24—C23—H23	120.7 (19)
C1—N2—C4—C3	0.7 (3)	C19—C14—C1—N2	31.2 (4)
C8—N2—C4—C3	169.6 (2)	C15—C14—C1—N2	−151.7 (2)
C1—N2—C4—C7	−178.7 (2)	C9—C8—C13—C12	−0.2 (4)
C8—N2—C4—C7	−9.8 (4)	N2—C8—C13—C12	178.1 (2)
N2—C4—C3—C2	−0.5 (3)	C19—C14—C15—C16	−0.8 (4)
C7—C4—C3—C2	178.9 (2)	C1—C14—C15—C16	−178.0 (2)
N2—C4—C3—C5	177.9 (2)	C20—N1—C6—C7	169.2 (2)
C7—C4—C3—C5	−2.7 (4)	C5—N1—C6—C7	−67.5 (3)
C4—N2—C8—C13	−115.3 (3)	C8—C13—C12—C11	−1.2 (4)
C1—N2—C8—C13	51.5 (4)	C3—C4—C7—C6	−13.6 (4)
C4—N2—C8—C9	63.1 (3)	N2—C4—C7—C6	165.6 (2)
C1—N2—C8—C9	−130.2 (3)	N1—C6—C7—C4	47.1 (3)
C15—C14—C19—C18	1.5 (4)	C18—C17—C16—C15	1.0 (4)
C1—C14—C19—C18	178.7 (2)	C14—C15—C16—C17	−0.5 (4)
C4—C3—C2—C1	0.1 (3)	C13—C8—C9—C10	0.9 (4)
C5—C3—C2—C1	−178.1 (3)	N2—C8—C9—C10	−177.4 (2)
C20—N1—C5—C3	170.0 (2)	C8—C9—C10—C11	−0.3 (4)
C6—N1—C5—C3	47.8 (3)	C9—C10—C11—F1	179.5 (3)
C4—C3—C5—N1	−14.0 (3)	C9—C10—C11—C12	−1.1 (5)
C2—C3—C5—N1	164.0 (2)	C13—C12—C11—C10	1.8 (5)
C5—N1—C20—C26	60.4 (3)	C13—C12—C11—F1	−178.7 (2)
C6—N1—C20—C26	−176.4 (3)	C16—C17—C18—C19	−0.2 (4)
C25—C26—C20—N1	−136.1 (3)	C14—C19—C18—C17	−1.1 (4)
C21—C26—C20—N1	45.7 (4)	C23—C22—C21—C26	−0.2 (5)
C3—C2—C1—N2	0.3 (3)	C25—C26—C21—C22	−0.4 (4)
C3—C2—C1—C14	176.8 (2)	C20—C26—C21—C22	177.8 (3)
C4—N2—C1—C2	−0.6 (3)	C21—C26—C25—C24	0.3 (5)
C8—N2—C1—C2	−168.9 (2)	C20—C26—C25—C24	−177.9 (3)
C4—N2—C1—C14	−177.2 (2)	C23—C24—C25—C26	0.3 (6)
C8—N2—C1—C14	14.5 (4)	C21—C22—C23—C24	0.9 (5)
C19—C14—C1—C2	−144.7 (3)	C25—C24—C23—C22	−0.9 (6)
C15—C14—C1—C2	32.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Cg1^i	0.95 (3)	2.79 (3)	3.648 (4)	150 (2)

Symmetry code: (i) −x, −y+1, −z+1.