1-Ethyl-3-(2-phenyl­ethyl)­benz­imidazole-2-selone

Öztürk, S.; Akkurt, M.; Büyükgüngör, O.; Küçükbay, H.; Orhan, E.

doi:10.1107/S1600536804014977

1-Ethyl-3-(2-phenylethyl)benzimidazole-2-selone

M. Akkurt, S. Öztürk, H. Küçükbay, E. Orhan and O. Büyükgüngör

The title compound, C₁₇H₁₈N₂Se, was synthesized by heating bis[1-ethyl-3-(2-phenylethyl)benzimidazolidin-2-ylidene] and selenium in toluene. The dihedral angle between the benzimidazole ring system and the phenyl ring is 17.2 (2)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804014977/ci6391sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804014977/ci6391Isup2.hkl Contains datablock I

CCDC reference: 245338

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.005 Å
R factor = 0.042
wR factor = 0.097
Data-to-parameter ratio = 20.9

checkCIF/PLATON results

No syntax errors found



Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.88
           From the CIF: _reflns_number_total               3831
           Count of symmetry unique reflns         2275
           Completeness (_total/calc)            168.40%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1556
           Fraction of Friedel pairs measured     0.684
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); 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-Ethyl-3-(2-phenylethyl)benzimidazole-2-selone top

Crystal data top

C₁₇H₁₈N₂Se	F(000) = 672
M_r = 329.29	D_x = 1.449 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2270 reflections
a = 7.6427 (5) Å	θ = 2.1–29.0°
b = 12.7380 (12) Å	µ = 2.48 mm⁻¹
c = 15.5045 (9) Å	T = 150 K
V = 1509.41 (19) Å³	Prism, colorless
Z = 4	0.31 × 0.26 × 0.22 mm

Data collection top

Stoe IPDS-II diffractometer	3831 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2914 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.087
Detector resolution: 6.67 pixels mm^-1	θ_max = 28.9°, θ_min = 2.1°
ω scans	h = −10→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −17→17
T_min = 0.514, T_max = 0.612	l = −19→21
13746 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.042	w = 1/[σ²(F_o²) + (0.0372P)² + 0.3896P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.097	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 0.50 e Å⁻³
3831 reflections	Δρ_min = −0.47 e Å⁻³
183 parameters	Extinction correction: SHELXL97, FC^*=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4
0 restraints	Extinction coefficient: 0.0095 (13)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983); 1584 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.288 (13)

Special details top

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} ^F2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of} ^F2 > 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} ^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

	x	y	z	U_iso*/U_eq
Se1	0.13218 (5)	0.48280 (3)	0.26723 (2)	0.0451 (1)
N1	−0.0856 (4)	0.3679 (2)	0.15037 (18)	0.0308 (8)
N2	0.0865 (3)	0.4791 (2)	0.08405 (16)	0.0293 (7)
C1	0.0413 (4)	0.4423 (3)	0.1633 (2)	0.0331 (10)
C2	−0.0090 (4)	0.4291 (3)	0.0209 (2)	0.0285 (10)
C3	−0.0069 (5)	0.4390 (3)	−0.0686 (2)	0.0342 (11)
C4	−0.1225 (6)	0.3767 (3)	−0.1134 (2)	0.0402 (11)
C5	−0.2372 (5)	0.3072 (3)	−0.0713 (3)	0.0420 (12)
C6	−0.2371 (5)	0.2976 (3)	0.0174 (3)	0.0387 (12)
C7	−0.1200 (5)	0.3594 (3)	0.0620 (2)	0.0304 (9)
C8	−0.1689 (5)	0.3058 (3)	0.2179 (2)	0.0387 (11)
C9	−0.3400 (5)	0.3510 (4)	0.2470 (3)	0.0540 (14)
C10	0.2266 (4)	0.5545 (3)	0.0694 (2)	0.0337 (11)
C11	0.4020 (4)	0.5007 (3)	0.0521 (2)	0.0371 (10)
C12	0.5525 (4)	0.5748 (3)	0.0603 (2)	0.0316 (10)
C13	0.5871 (5)	0.6200 (4)	0.1400 (3)	0.0430 (14)
C14	0.7233 (5)	0.6910 (4)	0.1509 (3)	0.0487 (14)
C15	0.8278 (5)	0.7174 (3)	0.0806 (3)	0.0397 (12)
C16	0.7946 (5)	0.6731 (3)	0.0021 (3)	0.0373 (11)
C17	0.6584 (5)	0.6019 (3)	−0.0085 (2)	0.0356 (11)
H3	0.06840	0.48520	−0.09650	0.0410*
H4	−0.12480	0.38060	−0.17330	0.0480*
H5	−0.31450	0.26700	−0.10380	0.0500*
H6	−0.31230	0.25160	0.04560	0.0460*
H8A	−0.09040	0.30120	0.26690	0.0470*
H8B	−0.18820	0.23510	0.19660	0.0470*
H9A	−0.38850	0.30760	0.29160	0.0810*
H9B	−0.41950	0.35380	0.19910	0.0810*
H9C	−0.32150	0.42060	0.26900	0.0810*
H10A	0.23770	0.59940	0.11970	0.0400*
H10B	0.19660	0.59850	0.02060	0.0400*
H11A	0.41720	0.44330	0.09260	0.0450*
H11B	0.40100	0.47120	−0.00560	0.0450*
H13	0.51760	0.60230	0.18700	0.0510*
H14	0.74450	0.72070	0.20470	0.0590*
H15	0.91940	0.76480	0.08700	0.0470*
H16	0.86390	0.69090	−0.04500	0.0450*
H17	0.63840	0.57210	−0.06240	0.0430*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se1	0.0498 (2)	0.0526 (2)	0.0329 (2)	−0.0068 (2)	−0.0097 (2)	−0.0008 (2)
N1	0.0305 (15)	0.0323 (15)	0.0297 (14)	−0.0035 (12)	0.0017 (12)	0.0007 (12)
N2	0.0267 (12)	0.0329 (13)	0.0283 (13)	−0.0023 (12)	−0.0034 (10)	0.0017 (13)
C1	0.0297 (17)	0.0330 (18)	0.0366 (19)	−0.0010 (15)	0.0014 (15)	0.0012 (15)
C2	0.0245 (15)	0.0317 (18)	0.0293 (17)	0.0014 (14)	−0.0008 (14)	0.0002 (14)
C3	0.0313 (17)	0.040 (2)	0.0312 (18)	−0.0023 (16)	0.0013 (15)	0.0029 (16)
C4	0.043 (2)	0.052 (2)	0.0256 (17)	0.000 (2)	0.0001 (18)	−0.0034 (15)
C5	0.045 (2)	0.044 (2)	0.037 (2)	−0.0127 (19)	−0.0019 (18)	−0.0065 (18)
C6	0.035 (2)	0.042 (2)	0.039 (2)	−0.0099 (17)	0.0083 (17)	−0.0062 (17)
C7	0.0290 (16)	0.0308 (16)	0.0314 (16)	−0.0010 (16)	0.0031 (16)	−0.0003 (13)
C8	0.039 (2)	0.0412 (19)	0.036 (2)	−0.0050 (16)	0.0044 (15)	0.0084 (16)
C9	0.044 (2)	0.075 (3)	0.043 (2)	0.004 (2)	0.0094 (19)	0.011 (2)
C10	0.0273 (16)	0.0358 (19)	0.038 (2)	−0.0058 (15)	−0.0032 (15)	0.0040 (15)
C11	0.0282 (16)	0.040 (2)	0.0432 (18)	−0.0025 (15)	−0.0060 (13)	−0.0014 (16)
C12	0.0269 (16)	0.0331 (19)	0.0347 (19)	−0.0006 (15)	−0.0031 (15)	0.0024 (15)
C13	0.035 (2)	0.058 (3)	0.036 (2)	−0.0133 (18)	−0.0012 (16)	0.0069 (18)
C14	0.044 (2)	0.067 (3)	0.035 (2)	−0.019 (2)	−0.0049 (18)	0.005 (2)
C15	0.031 (2)	0.042 (2)	0.046 (2)	−0.0103 (15)	−0.0054 (16)	0.0083 (17)
C16	0.0270 (17)	0.045 (2)	0.040 (2)	0.0041 (16)	0.0057 (16)	0.0060 (17)
C17	0.0319 (18)	0.0371 (18)	0.0379 (19)	0.0055 (16)	−0.0039 (15)	−0.0006 (15)

Geometric parameters (Å, º) top

Se1—C1	1.829 (3)	C15—C16	1.365 (6)
N1—C1	1.371 (4)	C16—C17	1.390 (5)
N1—C7	1.399 (4)	C3—H3	0.93
N1—C8	1.459 (4)	C4—H4	0.93
N2—C1	1.360 (4)	C5—H5	0.93
N2—C2	1.377 (4)	C6—H6	0.93
N2—C10	1.456 (4)	C8—H8A	0.97
C2—C3	1.394 (4)	C8—H8B	0.97
C2—C7	1.384 (5)	C9—H9A	0.96
C3—C4	1.376 (5)	C9—H9B	0.96
C4—C5	1.407 (6)	C9—H9C	0.96
C5—C6	1.381 (7)	C10—H10A	0.97
C6—C7	1.378 (5)	C10—H10B	0.97
C8—C9	1.498 (6)	C11—H11A	0.97
C10—C11	1.529 (5)	C11—H11B	0.97
C11—C12	1.493 (5)	C13—H13	0.93
C12—C13	1.389 (6)	C14—H14	0.93
C12—C17	1.383 (5)	C15—H15	0.93
C13—C14	1.389 (6)	C16—H16	0.93
C14—C15	1.393 (6)	C17—H17	0.93

Se1···H8A	2.8714	H4···C13^viii	2.9090
Se1···H10A	2.8440	H4···C14^viii	2.9712
Se1···H3ⁱ	3.1411	H4···H13^viii	2.3260
Se1···H8Bⁱⁱ	3.2903	H4···H14^viii	2.4657
N1···H5ⁱⁱⁱ	2.7869	H5···N1^ix	2.7869
C2···C17^iv	3.393 (5)	H5···C1^ix	3.0288
C2···C16^iv	3.464 (5)	H5···C7^ix	2.9093
C3···C17^iv	3.423 (5)	H6···C8	2.9689
C3···C16^iv	3.521 (5)	H6···H8B	2.5347
C15···C17^v	3.596 (5)	H6···C2^ix	2.9362
C16···C3^vi	3.521 (5)	H6···C3^ix	2.8694
C16···C2^vi	3.464 (5)	H6···C4^ix	3.0654
C17···C3^vi	3.423 (5)	H8A···Se1	2.8714
C17···C15^vii	3.596 (5)	H8B···C6	2.9143
C17···C2^vi	3.393 (5)	H8B···H6	2.5347
C1···H5ⁱⁱⁱ	3.0288	H8B···Se1^x	3.2903
C1···H11A	3.0749	H9A···H16ⁱ	2.5405
C2···H6ⁱⁱⁱ	2.9362	H9A···C13^x	3.0231
C3···H6ⁱⁱⁱ	2.8694	H9A···C14^x	3.0900
C3···H10B	2.9085	H9B···H11A^iv	2.3630
C4···H6ⁱⁱⁱ	3.0654	H10A···Se1	2.8440
C6···H8B	2.9143	H10A···C13	2.7016
C7···H5ⁱⁱⁱ	2.9093	H10A···H13	2.3804
C8···H6	2.9689	H10B···C3	2.9085
C10···H13	2.9397	H10B···H3	2.5178
C10···H3	2.9761	H10B···C15^vii	2.9944
C13···H9Aⁱⁱ	3.0231	H10B···C16^vii	3.0248
C13···H10A	2.7016	H11A···C1	3.0749
C13···H4ⁱ	2.9090	H11A···H9B^vi	2.3630
C14···H4ⁱ	2.9712	H11B···H17	2.3915
C14···H9Aⁱⁱ	3.0900	H13···C10	2.9397
C15···H10B^v	2.9944	H13···H10A	2.3804
C16···H10B^v	3.0248	H13···H4ⁱ	2.3260
C17···H15^vii	2.7751	H14···H4ⁱ	2.4657
H3···C10	2.9761	H15···C17^v	2.7751
H3···H10B	2.5178	H16···H9A^viii	2.5405
H3···Se1^viii	3.1411	H17···H11B	2.3915

C1—N1—C7	109.3 (3)	C6—C5—H5	119.42
C1—N1—C8	125.4 (3)	C5—C6—H6	121.59
C7—N1—C8	125.4 (3)	C7—C6—H6	121.70
C1—N2—C2	110.4 (3)	N1—C8—H8A	108.97
C1—N2—C10	123.7 (3)	N1—C8—H8B	108.99
C2—N2—C10	125.7 (3)	C9—C8—H8A	109.10
Se1—C1—N1	126.3 (2)	C9—C8—H8B	109.05
Se1—C1—N2	127.0 (2)	H8A—C8—H8B	107.73
N1—C1—N2	106.6 (3)	C8—C9—H9A	109.43
N2—C2—C3	131.3 (3)	C8—C9—H9B	109.49
N2—C2—C7	107.1 (3)	C8—C9—H9C	109.46
C3—C2—C7	121.6 (3)	H9A—C9—H9B	109.53
C2—C3—C4	116.3 (3)	H9A—C9—H9C	109.43
C3—C4—C5	121.9 (3)	H9B—C9—H9C	109.49
C4—C5—C6	121.2 (4)	N2—C10—H10A	109.12
C5—C6—C7	116.7 (4)	N2—C10—H10B	109.22
N1—C7—C2	106.6 (3)	C11—C10—H10A	109.17
N1—C7—C6	131.1 (3)	C11—C10—H10B	109.25
C2—C7—C6	122.3 (3)	H10A—C10—H10B	107.89
N1—C8—C9	112.9 (3)	C10—C11—H11A	109.21
N2—C10—C11	112.1 (3)	C10—C11—H11B	109.17
C10—C11—C12	112.2 (3)	C12—C11—H11A	109.20
C11—C12—C13	119.0 (3)	C12—C11—H11B	109.23
C11—C12—C17	122.9 (3)	H11A—C11—H11B	107.80
C13—C12—C17	118.1 (3)	C12—C13—H13	119.22
C12—C13—C14	121.4 (4)	C14—C13—H13	119.39
C13—C14—C15	119.5 (4)	C13—C14—H14	120.29
C14—C15—C16	119.4 (4)	C15—C14—H14	120.25
C15—C16—C17	120.9 (4)	C14—C15—H15	120.34
C12—C17—C16	120.7 (3)	C16—C15—H15	120.23
C2—C3—H3	121.85	C15—C16—H16	119.56
C4—C3—H3	121.85	C17—C16—H16	119.51
C3—C4—H4	119.04	C12—C17—H17	119.66
C5—C4—H4	119.02	C16—C17—H17	119.69
C4—C5—H5	119.40

C7—N1—C1—Se1	179.9 (3)	N2—C2—C7—N1	−1.1 (4)
C8—N1—C1—Se1	−1.3 (5)	N2—C2—C7—C6	178.7 (3)
C7—N1—C1—N2	−0.5 (4)	N2—C2—C3—C4	−179.5 (4)
C8—N1—C1—N2	178.3 (3)	C7—C2—C3—C4	0.8 (5)
C8—N1—C7—C6	2.4 (6)	C3—C2—C7—C6	−1.4 (6)
C1—N1—C8—C9	96.3 (4)	C2—C3—C4—C5	0.3 (6)
C7—N1—C8—C9	−85.1 (4)	C3—C4—C5—C6	−0.8 (6)
C1—N1—C7—C6	−178.8 (4)	C4—C5—C6—C7	0.2 (6)
C1—N1—C7—C2	1.0 (4)	C5—C6—C7—C2	0.9 (6)
C8—N1—C7—C2	−177.8 (3)	C5—C6—C7—N1	−179.3 (4)
C10—N2—C1—N1	−175.6 (3)	N2—C10—C11—C12	−164.8 (3)
C2—N2—C1—Se1	179.4 (3)	C10—C11—C12—C13	63.8 (4)
C10—N2—C1—Se1	4.0 (5)	C10—C11—C12—C17	−115.3 (4)
C2—N2—C1—N1	−0.2 (4)	C17—C12—C13—C14	0.4 (6)
C1—N2—C10—C11	91.3 (4)	C11—C12—C17—C16	178.6 (3)
C2—N2—C10—C11	−83.4 (4)	C11—C12—C13—C14	−178.7 (4)
C1—N2—C2—C3	−179.0 (4)	C13—C12—C17—C16	−0.5 (6)
C10—N2—C2—C3	−3.7 (6)	C12—C13—C14—C15	−0.1 (7)
C1—N2—C2—C7	0.9 (4)	C13—C14—C15—C16	0.0 (6)
C10—N2—C2—C7	176.1 (3)	C14—C15—C16—C17	−0.2 (6)
C3—C2—C7—N1	178.7 (3)	C15—C16—C17—C12	0.4 (6)

Symmetry codes: (i) −x+1/2, −y+1, z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) x+1/2, −y+1/2, −z; (iv) x−1, y, z; (v) x+1/2, −y+3/2, −z; (vi) x+1, y, z; (vii) x−1/2, −y+3/2, −z; (viii) −x+1/2, −y+1, z−1/2; (ix) x−1/2, −y+1/2, −z; (x) −x, y−1/2, −z+1/2.

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1-Ethyl-3-(2-phenyl­ethyl)­benz­imidazole-2-selone

Supporting information

Key indicators

checkCIF/PLATON results

1-Ethyl-3-(2-phenylethyl)benzimidazole-2-selone