1-(2-Piperidinoethyl)-1H-benz­imidazole

The title compound, C₁₄H₁₉N₃, was synthesized from benz­imidazole and N-(2-chloro­ethyl)­piperidine hydro­chloride in KOH/EtOH solution. The benz­imidazole ring is connected to the piperidine ring by an ethylene group. The piperidine ring displays a chair conformation.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.105
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         44 Perc.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1     -   C7      ..       6.89 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N3     -   C10     ..       5.69 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N3     -   C14     ..       6.92 su
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C13
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         N3

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

1-(2-piperidinoethyl)benzimidazole

Crystal data

C14H19N3	F(000) = 496
Mr = 229.32	Dx = 1.152 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3947 reflections
a = 6.3741 (8) Å	θ = 2.1–24.6°
b = 19.042 (2) Å	µ = 0.07 mm^−1
c = 11.1476 (14) Å	T = 293 K
β = 102.178 (10)°	Block, yellow
V = 1322.6 (3) Å^3	0.42 × 0.33 × 0.24 mm
Z = 4

Data collection

Stoe IPDS-II diffractometer	2596 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1132 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.050
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 2.1°
ω scans	h = −7→7
Absorption correction: integration (XRED32; Stoe & Cie, 2002)	k = −23→23
Tmin = 0.963, Tmax = 0.981	l = −13→13
9349 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters not refined
wR(F^2) = 0.105	w = 1/[σ^2(Fo^2) + (0.0515P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.80	(Δ/σ)max < 0.001
2596 reflections	Δρmax = 0.10 e Å^−3
155 parameters	Δρmin = −0.08 e Å^−3
0 restraints	Extinction correction: SHELXL97, FC^*=KFC[1+0.001XFC^2Λ^3/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.037 (3)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^{2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F}2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of F}2 > σ(F^{2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F}2 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	0.5213 (3)	0.20139 (10)	0.7011 (2)	0.0991 (8)
N2	0.8079 (2)	0.20143 (8)	0.61480 (15)	0.0725 (6)
N3	0.7442 (2)	0.11540 (8)	0.39174 (13)	0.0720 (6)
C1	0.8709 (3)	0.16764 (9)	0.72534 (18)	0.0661 (7)
C2	1.0610 (3)	0.13715 (11)	0.78226 (18)	0.0797 (8)
C3	1.0675 (4)	0.10635 (12)	0.8943 (2)	0.0935 (9)
C4	0.8900 (4)	0.10689 (12)	0.9485 (2)	0.0950 (10)
C5	0.7029 (4)	0.13780 (12)	0.8924 (2)	0.0930 (10)
C6	0.6908 (3)	0.16862 (10)	0.7779 (2)	0.0755 (8)
C7	0.5997 (3)	0.21922 (11)	0.6064 (2)	0.0920 (9)
C8	0.9332 (3)	0.20995 (11)	0.52046 (18)	0.0855 (8)
C9	0.9522 (3)	0.14236 (12)	0.45334 (18)	0.0882 (9)
C10	0.6650 (4)	0.14823 (12)	0.27386 (19)	0.0987 (10)
C11	0.4419 (4)	0.12558 (14)	0.2182 (2)	0.1124 (11)
C12	0.4257 (4)	0.04738 (15)	0.2065 (2)	0.1230 (11)
C13	0.5193 (5)	0.01417 (14)	0.3281 (2)	0.1381 (14)
C14	0.7407 (4)	0.04024 (13)	0.3791 (2)	0.1162 (11)
H2	1.18030	0.13740	0.74650	0.0960*
H3	1.19320	0.08470	0.93480	0.1120*
H4	0.89960	0.08570	1.02460	0.1140*
H5	0.58540	0.13830	0.92960	0.1120*
H7	0.51900	0.24230	0.53860	0.1100*
H8A	1.07560	0.22660	0.55820	0.1030*
H8B	0.86570	0.24520	0.46210	0.1030*
H9A	1.03970	0.15030	0.39320	0.1060*
H9B	1.02390	0.10760	0.51130	0.1060*
H10A	0.75880	0.13620	0.21880	0.1180*
H10B	0.66800	0.19880	0.28400	0.1180*
H11A	0.39770	0.14670	0.13760	0.1350*
H11B	0.34540	0.14200	0.26880	0.1350*
H12A	0.50300	0.03140	0.14530	0.1470*
H12B	0.27650	0.03370	0.18010	0.1470*
H13A	0.42830	0.02460	0.38550	0.1660*
H13B	0.52290	−0.03640	0.31830	0.1660*
H14A	0.79430	0.01890	0.45870	0.1390*
H14B	0.83470	0.02640	0.32520	0.1390*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0729 (11)	0.0975 (14)	0.1348 (16)	0.0094 (10)	0.0397 (12)	0.0040 (12)
N2	0.0587 (9)	0.0724 (11)	0.0872 (11)	−0.0055 (8)	0.0175 (8)	−0.0073 (9)
N3	0.0814 (11)	0.0688 (11)	0.0633 (9)	0.0070 (9)	0.0096 (8)	0.0058 (8)
C1	0.0576 (11)	0.0648 (12)	0.0762 (12)	−0.0085 (9)	0.0150 (10)	−0.0148 (10)
C2	0.0625 (13)	0.1007 (16)	0.0766 (14)	−0.0050 (11)	0.0161 (10)	−0.0135 (12)
C3	0.0789 (14)	0.1176 (19)	0.0792 (14)	−0.0053 (12)	0.0058 (12)	−0.0101 (13)
C4	0.0992 (17)	0.1098 (19)	0.0792 (14)	−0.0149 (14)	0.0262 (14)	−0.0125 (12)
C5	0.0894 (16)	0.0978 (17)	0.1030 (17)	−0.0148 (14)	0.0459 (14)	−0.0229 (14)
C6	0.0644 (13)	0.0701 (13)	0.0971 (15)	−0.0067 (11)	0.0286 (12)	−0.0162 (11)
C7	0.0698 (14)	0.0787 (15)	0.1242 (19)	0.0058 (12)	0.0132 (13)	0.0056 (13)
C8	0.0739 (13)	0.0927 (16)	0.0905 (14)	−0.0149 (11)	0.0187 (11)	0.0038 (12)
C9	0.0748 (13)	0.1112 (18)	0.0818 (14)	0.0083 (12)	0.0240 (11)	−0.0016 (12)
C10	0.123 (2)	0.0841 (16)	0.0821 (14)	−0.0036 (13)	0.0059 (13)	0.0149 (12)
C11	0.128 (2)	0.100 (2)	0.0911 (16)	0.0035 (16)	−0.0177 (14)	0.0067 (13)
C12	0.144 (2)	0.098 (2)	0.1082 (19)	−0.0128 (17)	−0.0158 (16)	−0.0013 (15)
C13	0.170 (3)	0.0879 (19)	0.132 (2)	−0.0327 (18)	−0.0233 (19)	0.0279 (16)
C14	0.136 (2)	0.0816 (18)	0.1157 (18)	0.0140 (16)	−0.0078 (16)	0.0131 (14)

Geometric parameters (Å, º)

N1—C6	1.378 (3)	C2—H2	0.9301
N1—C7	1.305 (3)	C3—H3	0.9291
N2—C1	1.373 (3)	C4—H4	0.9297
N2—C7	1.354 (2)	C5—H5	0.9295
N2—C8	1.458 (2)	C7—H7	0.9300
N3—C9	1.452 (2)	C8—H8A	0.9697
N3—C10	1.447 (3)	C8—H8B	0.9700
N3—C14	1.438 (3)	C9—H9A	0.9701
C1—C2	1.372 (3)	C9—H9B	0.9695
C1—C6	1.395 (3)	C10—H10A	0.9703
C2—C3	1.373 (3)	C10—H10B	0.9693
C3—C4	1.391 (4)	C11—H11A	0.9704
C4—C5	1.358 (3)	C11—H11B	0.9699
C5—C6	1.392 (3)	C12—H12A	0.9709
C8—C9	1.506 (3)	C12—H12B	0.9700
C10—C11	1.490 (4)	C13—H13A	0.9705
C11—C12	1.497 (4)	C13—H13B	0.9699
C12—C13	1.501 (3)	C14—H14A	0.9702
C13—C14	1.491 (4)	C14—H14B	0.9702
N1···N2	2.237 (2)	H8B···H7	2.5316
N2···N1	2.237 (2)	H8B···H10B	2.2924
N2···N3	2.934 (2)	H9A···H10A	2.3641
N3···N2	2.934 (2)	H9A···H10B	2.5945
N3···C7	3.378 (3)	H9B···C1	2.9888
N1···H2^i	2.6324	H9B···C2	3.0323
N2···H11A^ii	2.9486	H9B···H14A	2.2308
C2···C9	3.586 (3)	H10A···H9A	2.3641
C7···N3	3.378 (3)	H10A···H12A	2.5978
C9···C2	3.586 (3)	H10A···H14B	2.4021
C1···H9B	2.9888	H10B···C8	2.8233
C2···H8A	3.0408	H10B···H8B	2.2924
C2···H9B	3.0323	H10B···H9A	2.5945
C4···H7^ii	3.0957	H11A···N2^v	2.9486
C6···H13B^iii	2.9543	H11A···C8^v	3.0549
C8···H10B	2.8233	H11B···H13A	2.5844
C8···H11A^ii	3.0549	H12A···H10A	2.5978
C8···H2	3.0107	H12A···H14B	2.5908
C10···H8B	2.8839	H13A···H11B	2.5844
H2···N1^iv	2.6324	H13A···H14A^iii	2.5991
H2···C8	3.0107	H13B···C6^iii	2.9543
H7···H8B	2.5316	H14A···H9B	2.2308
H7···C4^v	3.0957	H14A···H13A^iii	2.5991
H8A···C2	3.0408	H14B···H10A	2.4021
H8B···C10	2.8839	H14B···H12A	2.5908
C6—N1—C7	103.69 (18)	N2—C8—H8A	109.18
C1—N2—C7	106.04 (16)	N2—C8—H8B	109.14
C1—N2—C8	126.78 (15)	C9—C8—H8A	109.20
C7—N2—C8	126.92 (17)	C9—C8—H8B	109.20
C9—N3—C10	112.68 (16)	H8A—C8—H8B	107.87
C9—N3—C14	113.08 (16)	N3—C9—H9A	109.20
C10—N3—C14	110.24 (16)	N3—C9—H9B	109.20
N2—C1—C2	132.51 (18)	C8—C9—H9A	109.16
N2—C1—C6	105.07 (16)	C8—C9—H9B	109.16
C2—C1—C6	122.42 (18)	H9A—C9—H9B	107.94
C1—C2—C3	117.11 (19)	N3—C10—H10A	109.21
C2—C3—C4	121.4 (2)	N3—C10—H10B	109.20
C3—C4—C5	121.3 (2)	C11—C10—H10A	109.24
C4—C5—C6	118.6 (2)	C11—C10—H10B	109.25
N1—C6—C1	110.61 (19)	H10A—C10—H10B	107.98
N1—C6—C5	130.2 (2)	C10—C11—H11A	109.31
C1—C6—C5	119.22 (19)	C10—C11—H11B	109.34
N1—C7—N2	114.60 (19)	C12—C11—H11A	109.30
N2—C8—C9	112.15 (16)	C12—C11—H11B	109.32
N3—C9—C8	112.08 (16)	H11A—C11—H11B	108.00
N3—C10—C11	111.88 (19)	C11—C12—H12A	109.71
C10—C11—C12	111.5 (2)	C11—C12—H12B	109.81
C11—C12—C13	109.5 (2)	C13—C12—H12A	109.80
C12—C13—C14	111.6 (2)	C13—C12—H12B	109.78
N3—C14—C13	111.3 (2)	H12A—C12—H12B	108.24
C1—C2—H2	121.44	C12—C13—H13A	109.29
C3—C2—H2	121.45	C12—C13—H13B	109.33
C2—C3—H3	119.29	C14—C13—H13A	109.25
C4—C3—H3	119.31	C14—C13—H13B	109.30
C3—C4—H4	119.36	H13A—C13—H13B	108.00
C5—C4—H4	119.38	N3—C14—H14A	109.39
C4—C5—H5	120.72	N3—C14—H14B	109.40
C6—C5—H5	120.71	C13—C14—H14A	109.37
N1—C7—H7	122.68	C13—C14—H14B	109.39
N2—C7—H7	122.72	H14A—C14—H14B	107.96
C7—N1—C6—C1	−0.1 (2)	C2—C1—C6—C5	0.1 (3)
C7—N1—C6—C5	−179.2 (2)	C6—C1—C2—C3	0.7 (3)
C6—N1—C7—N2	−0.5 (2)	N2—C1—C6—C5	179.89 (18)
C8—N2—C1—C6	−175.28 (17)	N2—C1—C6—N1	0.7 (2)
C8—N2—C7—N1	175.30 (18)	C2—C1—C6—N1	−179.09 (18)
C1—N2—C8—C9	72.8 (2)	N2—C1—C2—C3	−179.0 (2)
C7—N2—C8—C9	−100.4 (2)	C1—C2—C3—C4	−0.9 (3)
C7—N2—C1—C6	−0.9 (2)	C2—C3—C4—C5	0.2 (4)
C7—N2—C1—C2	178.8 (2)	C3—C4—C5—C6	0.7 (3)
C8—N2—C1—C2	4.4 (3)	C4—C5—C6—C1	−0.8 (3)
C1—N2—C7—N1	1.0 (2)	C4—C5—C6—N1	178.2 (2)
C14—N3—C9—C8	−151.69 (17)	N2—C8—C9—N3	60.4 (2)
C10—N3—C9—C8	82.5 (2)	N3—C10—C11—C12	−56.0 (2)
C10—N3—C14—C13	−59.1 (2)	C10—C11—C12—C13	52.1 (3)
C9—N3—C10—C11	−173.87 (18)	C11—C12—C13—C14	−52.8 (3)
C14—N3—C10—C11	58.8 (2)	C12—C13—C14—N3	57.2 (3)
C9—N3—C14—C13	173.74 (17)

Symmetry codes: (i) x−1, y, z; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x+1, −y, −z+1; (iv) x+1, y, z; (v) x−1/2, −y+1/2, z−1/2.