6-Nitro-1-(2-phenyl­eth­yl)-1H-benzimidazole

The title compound, C₁₅H₁₃N₃O₂, was synthesized from 5-nitro­benzimidazole, 2-bromo­ethyl­benzene and KOH in ethanol. The phen­yl and benzimidazole ring systems are each planar and make a dihedral angle of 43.9 (1)°. The crystal structure is stabilized by weak inter­molecular C—H...N hydrogen-bond inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.113
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.54 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N3     -   C4      ..       6.06 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C10    -   C11     ..       6.73 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C11    -   C12     ..       6.92 su

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

   1 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
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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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: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

6-Nitro-1-(2-phenylethyl)-1H-benzimidazole

Crystal data

C15H13N3O2	F(000) = 560
Mr = 267.28	Dx = 1.340 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11275 reflections
a = 6.6382 (6) Å	θ = 2.1–28.0°
b = 11.4258 (6) Å	µ = 0.09 mm^−1
c = 18.2702 (16) Å	T = 296 K
β = 107.039 (7)°	Prism, colorless
V = 1324.91 (19) Å^3	0.40 × 0.26 × 0.09 mm
Z = 4

Data collection

Stoe IPDS-II diffractometer	2570 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1674 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.089
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 2.1°
ω scans	h = −8→7
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −14→14
Tmin = 0.971, Tmax = 0.992	l = −22→22
14688 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)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.113	w = 1/[σ^2(Fo^2) + (0.0641P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.93	(Δ/σ)max = 0.001
2570 reflections	Δρmax = 0.12 e Å^−3
182 parameters	Δρmin = −0.14 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: 0.008 (2)

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 F² 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 F². The observed criterion of F² > σ(F²) 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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.5397 (2)	0.24673 (14)	0.67652 (7)	0.0910 (6)
O2	0.2466 (3)	0.28135 (15)	0.59085 (8)	0.0906 (6)
N1	0.7196 (2)	0.05178 (14)	0.38204 (8)	0.0668 (6)
N2	0.3718 (2)	0.08776 (11)	0.35325 (6)	0.0513 (4)
N3	0.4263 (3)	0.24378 (13)	0.61029 (8)	0.0639 (5)
C1	0.6745 (3)	0.09986 (13)	0.44519 (9)	0.0534 (5)
C2	0.8095 (3)	0.12279 (15)	0.51789 (10)	0.0635 (6)
C3	0.7251 (3)	0.16928 (15)	0.57105 (9)	0.0610 (6)
C4	0.5111 (3)	0.19340 (13)	0.55199 (8)	0.0507 (5)
C5	0.3709 (3)	0.17203 (13)	0.48051 (8)	0.0494 (5)
C6	0.4596 (2)	0.12379 (12)	0.42813 (7)	0.0459 (5)
C7	0.5344 (3)	0.04725 (15)	0.33028 (10)	0.0628 (6)
C8	0.1497 (3)	0.08718 (16)	0.30919 (8)	0.0601 (6)
C9	0.0789 (3)	0.19722 (18)	0.26334 (9)	0.0727 (7)
C10	0.1051 (3)	0.30562 (16)	0.31172 (9)	0.0644 (6)
C11	0.2856 (4)	0.3712 (2)	0.32642 (13)	0.0869 (9)
C12	0.3164 (5)	0.4663 (2)	0.37383 (17)	0.1130 (11)
C13	0.1647 (7)	0.4982 (2)	0.40753 (16)	0.1164 (13)
C14	−0.0161 (5)	0.4348 (2)	0.39367 (14)	0.1036 (13)
C15	−0.0454 (4)	0.33838 (19)	0.34612 (11)	0.0784 (8)
H2	0.95280	0.10690	0.52980	0.0760*
H3	0.81110	0.18490	0.62020	0.0730*
H5	0.22790	0.18890	0.46880	0.0590*
H7	0.51660	0.01820	0.28130	0.0750*
H8A	0.06550	0.07660	0.34400	0.0720*
H8B	0.12360	0.02080	0.27460	0.0720*
H9A	0.15900	0.20620	0.22700	0.0870*
H9B	−0.06840	0.18910	0.23440	0.0870*
H11	0.38900	0.35050	0.30370	0.1040*
H12	0.44010	0.50950	0.38330	0.1350*
H13	0.18560	0.56290	0.43970	0.1400*
H14	−0.11950	0.45630	0.41610	0.1250*
H15	−0.16870	0.29490	0.33710	0.0940*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0916 (11)	0.1255 (12)	0.0500 (7)	−0.0192 (9)	0.0116 (7)	−0.0236 (7)
O2	0.0798 (11)	0.1202 (12)	0.0732 (8)	0.0178 (9)	0.0245 (7)	−0.0241 (8)
N1	0.0615 (10)	0.0739 (10)	0.0737 (9)	0.0084 (7)	0.0332 (8)	−0.0003 (7)
N2	0.0554 (8)	0.0549 (8)	0.0454 (6)	0.0045 (6)	0.0175 (6)	−0.0008 (5)
N3	0.0696 (10)	0.0669 (9)	0.0549 (8)	−0.0095 (8)	0.0176 (7)	−0.0108 (7)
C1	0.0517 (10)	0.0496 (9)	0.0610 (9)	0.0008 (7)	0.0199 (7)	0.0040 (7)
C2	0.0447 (10)	0.0642 (11)	0.0772 (11)	0.0001 (8)	0.0110 (8)	−0.0004 (8)
C3	0.0545 (11)	0.0610 (10)	0.0594 (9)	−0.0065 (8)	0.0041 (8)	−0.0034 (7)
C4	0.0575 (10)	0.0451 (8)	0.0494 (8)	−0.0056 (7)	0.0153 (7)	−0.0043 (6)
C5	0.0467 (9)	0.0504 (8)	0.0508 (8)	0.0015 (7)	0.0140 (6)	0.0007 (6)
C6	0.0509 (9)	0.0426 (8)	0.0451 (7)	−0.0005 (6)	0.0153 (6)	0.0033 (6)
C7	0.0704 (12)	0.0655 (11)	0.0594 (9)	0.0080 (9)	0.0298 (9)	−0.0007 (8)
C8	0.0576 (11)	0.0704 (11)	0.0493 (8)	−0.0015 (8)	0.0109 (7)	−0.0071 (7)
C9	0.0717 (13)	0.0927 (14)	0.0507 (9)	0.0135 (10)	0.0132 (8)	0.0082 (9)
C10	0.0690 (12)	0.0657 (11)	0.0575 (9)	0.0127 (9)	0.0169 (8)	0.0208 (8)
C11	0.0994 (18)	0.0679 (13)	0.0980 (14)	0.0034 (12)	0.0359 (12)	0.0229 (12)
C12	0.126 (2)	0.0732 (16)	0.135 (2)	−0.0193 (15)	0.0310 (19)	0.0204 (16)
C13	0.177 (3)	0.0632 (14)	0.1072 (19)	0.0044 (19)	0.039 (2)	0.0039 (13)
C14	0.139 (3)	0.0865 (17)	0.0965 (16)	0.0360 (17)	0.0520 (16)	0.0158 (14)
C15	0.0838 (14)	0.0806 (14)	0.0740 (11)	0.0174 (11)	0.0280 (10)	0.0133 (10)

Geometric parameters (Å, º)

O1—N3	1.2240 (19)	C11—C12	1.367 (3)
O2—N3	1.219 (3)	C12—C13	1.375 (5)
N1—C1	1.388 (2)	C13—C14	1.361 (5)
N1—C7	1.314 (2)	C14—C15	1.381 (3)
N2—C6	1.3833 (16)	C2—H2	0.9300
N2—C7	1.349 (2)	C3—H3	0.9300
N2—C8	1.458 (2)	C5—H5	0.9300
N3—C4	1.461 (2)	C7—H7	0.9300
C1—C2	1.392 (2)	C8—H8A	0.9700
C1—C6	1.395 (2)	C8—H8B	0.9700
C2—C3	1.363 (3)	C9—H9A	0.9700
C3—C4	1.388 (3)	C9—H9B	0.9700
C4—C5	1.385 (2)	C11—H11	0.9300
C5—C6	1.377 (2)	C12—H12	0.9300
C8—C9	1.508 (3)	C13—H13	0.9300
C9—C10	1.502 (3)	C14—H14	0.9300
C10—C11	1.371 (3)	C15—H15	0.9300
C10—C15	1.379 (3)
O1···C7^i	3.392 (2)	C5···H8A	2.9300
O2···C2^ii	3.348 (3)	C8···H5	3.0400
O1···H9B^iii	2.6100	C9···H3^viii	3.0100
O1···H3	2.4300	C10···H5	3.0500
O2···H2^ii	2.7800	C10···H8B^ix	3.0700
O2···H5	2.4400	C15···H5	2.9700
O2···H9A^iv	2.7200	C15···H8A	3.0800
N1···N2	2.250 (2)	C15···H8B^ix	2.9700
N2···C11	3.300 (3)	H2···O2^v	2.7800
N2···C3^i	3.387 (2)	H2···H5^v	2.5800
N2···N1	2.250 (2)	H2···N1^vi	2.9300
N1···H8A^v	2.6000	H3···O1	2.4300
N1···H2^vi	2.9300	H3···C9^iii	3.0100
N3···H12^vii	2.9500	H3···H9B^iii	2.4700
C1···C4^i	3.576 (2)	H5···O2	2.4400
C1···C5^i	3.439 (2)	H5···C8	3.0400
C2···O2^v	3.348 (3)	H5···C10	3.0500
C2···C5^i	3.578 (2)	H5···C15	2.9700
C3···N2^i	3.387 (2)	H5···H2^ii	2.5800
C3···C6^i	3.568 (2)	H5···H8A	2.5600
C4···C1^i	3.576 (2)	H7···H8B	2.5800
C4···C7^i	3.558 (2)	H8A···N1^ii	2.6000
C5···C10	3.430 (2)	H8A···C5	2.9300
C5···C11	3.534 (3)	H8A···C15	3.0800
C5···C1^i	3.439 (2)	H8A···H5	2.5600
C5···C2^i	3.578 (2)	H8B···H7	2.5800
C6···C10	3.383 (2)	H8B···C10^x	3.0700
C6···C11	3.394 (3)	H8B···C15^x	2.9700
C6···C3^i	3.568 (2)	H9A···H11	2.4000
C7···C4^i	3.558 (2)	H9A···O2^xi	2.7200
C7···O1^i	3.392 (2)	H9B···H15	2.4800
C10···C5	3.430 (2)	H9B···O1^viii	2.6100
C10···C6	3.383 (2)	H9B···H3^viii	2.4700
C11···C6	3.394 (3)	H11···H9A	2.4000
C11···C5	3.534 (3)	H12···N3^vii	2.9500
C11···N2	3.300 (3)	H15···H9B	2.4800
C1—N1—C7	103.28 (15)	C10—C15—C14	121.1 (2)
C6—N2—C7	105.43 (13)	C1—C2—H2	121.00
C6—N2—C8	127.75 (13)	C3—C2—H2	121.00
C7—N2—C8	126.75 (13)	C2—C3—H3	120.00
O1—N3—O2	122.98 (17)	C4—C3—H3	120.00
O1—N3—C4	118.35 (17)	C4—C5—H5	123.00
O2—N3—C4	118.67 (14)	C6—C5—H5	123.00
N1—C1—C2	129.23 (18)	N1—C7—H7	122.00
N1—C1—C6	110.33 (14)	N2—C7—H7	122.00
C2—C1—C6	120.43 (16)	N2—C8—H8A	109.00
C1—C2—C3	117.97 (18)	N2—C8—H8B	109.00
C2—C3—C4	120.19 (16)	C9—C8—H8A	109.00
N3—C4—C3	118.70 (14)	C9—C8—H8B	109.00
N3—C4—C5	117.44 (17)	H8A—C8—H8B	108.00
C3—C4—C5	123.86 (16)	C8—C9—H9A	109.00
C4—C5—C6	114.82 (17)	C8—C9—H9B	109.00
N2—C6—C1	105.64 (12)	C10—C9—H9A	109.00
N2—C6—C5	131.63 (14)	C10—C9—H9B	109.00
C1—C6—C5	122.72 (13)	H9A—C9—H9B	108.00
N1—C7—N2	115.31 (15)	C10—C11—H11	119.00
N2—C8—C9	113.77 (15)	C12—C11—H11	119.00
C8—C9—C10	113.41 (13)	C11—C12—H12	120.00
C9—C10—C11	120.65 (19)	C13—C12—H12	120.00
C9—C10—C15	121.18 (18)	C12—C13—H13	120.00
C11—C10—C15	118.07 (19)	C14—C13—H13	120.00
C10—C11—C12	121.2 (3)	C13—C14—H14	120.00
C11—C12—C13	120.1 (3)	C15—C14—H14	120.00
C12—C13—C14	119.8 (2)	C10—C15—H15	119.00
C13—C14—C15	119.7 (3)	C14—C15—H15	119.00
C7—N1—C1—C2	178.29 (17)	N1—C1—C6—C5	−180.00 (15)
C7—N1—C1—C6	−0.58 (18)	C1—C2—C3—C4	−0.6 (3)
C1—N1—C7—N2	0.0 (2)	C2—C3—C4—C5	0.6 (3)
C8—N2—C7—N1	−176.48 (15)	C2—C3—C4—N3	−179.68 (15)
C7—N2—C6—C1	−0.82 (16)	N3—C4—C5—C6	−179.56 (13)
C6—N2—C7—N1	0.52 (19)	C3—C4—C5—C6	0.1 (2)
C7—N2—C6—C5	−179.83 (16)	C4—C5—C6—C1	−0.9 (2)
C8—N2—C6—C5	−2.9 (3)	C4—C5—C6—N2	177.92 (15)
C8—N2—C6—C1	176.13 (14)	N2—C8—C9—C10	−60.6 (2)
C7—N2—C8—C9	−91.53 (19)	C8—C9—C10—C11	92.3 (2)
C6—N2—C8—C9	92.14 (18)	C8—C9—C10—C15	−83.9 (2)
O1—N3—C4—C5	169.00 (16)	C9—C10—C11—C12	−176.3 (2)
O1—N3—C4—C3	−10.7 (2)	C15—C10—C11—C12	0.1 (3)
O2—N3—C4—C5	−11.3 (2)	C9—C10—C15—C14	176.72 (19)
O2—N3—C4—C3	168.99 (17)	C11—C10—C15—C14	0.4 (3)
C6—C1—C2—C3	−0.2 (2)	C10—C11—C12—C13	−0.3 (4)
N1—C1—C2—C3	−178.99 (17)	C11—C12—C13—C14	0.1 (4)
C2—C1—C6—C5	1.0 (2)	C12—C13—C14—C15	0.4 (4)
C2—C1—C6—N2	−178.09 (14)	C13—C14—C15—C10	−0.6 (3)
N1—C1—C6—N2	0.90 (17)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···N1^ii	0.97	2.60	3.509 (2)	156

Symmetry code: (ii) x−1, y, z.