1-Methoxy­ethyl-5-nitro­benzimidazole

The title compound, C₁₀H₁₁N₃O₃, was synthesized by the reaction of 5-nitro­benzimidazole, 2-chloro­ethyl methyl ether and KOH in ethanol. The bond lengths and angles are unexceptional.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.049
• wR factor = 0.124
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.80 mm
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT411_ALERT_2_C Short Inter H...H Contact  H2     ..  H2      ..       2.14 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   2 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

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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); software used to prepare material for publication: WinGX (Farrugia, 1999).

1-Methoxyethyl-5-nitrobenzimidazole

Crystal data

C10H11N3O3	Z = 2
Mr = 221.22	F(000) = 232
Triclinic, P1	Dx = 1.399 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.7940 (7) Å	Cell parameters from 7061 reflections
b = 8.4531 (13) Å	θ = 2.7–27.9°
c = 13.411 (2) Å	µ = 0.11 mm^−1
α = 97.350 (12)°	T = 296 K
β = 94.854 (12)°	Plate, colorless
γ = 101.266 (12)°	0.80 × 0.37 × 0.05 mm
V = 525.25 (14) Å^3

Data collection

Stoe IPDS-II diffractometer	2443 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1327 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.049
Detector resolution: 6.67 pixels mm^-1	θmax = 27.7°, θmin = 2.5°
ω scans	h = −6→6
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −11→11
Tmin = 0.920, Tmax = 0.995	l = −17→17
8616 measured reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.124	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0607P)^2] where P = (Fo^2 + 2Fc^2)/3
2443 reflections	(Δ/σ)max < 0.001
178 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−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 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	0.6727 (5)	0.7623 (3)	0.40810 (15)	0.1142 (9)
O2	0.2956 (4)	0.5922 (3)	0.42843 (12)	0.1031 (8)
O3	0.2278 (4)	0.47209 (17)	0.89320 (11)	0.0773 (6)
N1	0.4909 (5)	0.7079 (3)	0.46004 (14)	0.0760 (7)
N2	0.5574 (4)	0.9718 (2)	0.86513 (13)	0.0683 (6)
N3	0.1970 (3)	0.75853 (18)	0.80550 (11)	0.0543 (5)
C1	0.5115 (5)	0.7834 (2)	0.56586 (14)	0.0594 (7)
C2	0.7353 (6)	0.9169 (3)	0.60125 (18)	0.0706 (8)
C3	0.7654 (5)	0.9889 (3)	0.70051 (18)	0.0697 (8)
C4	0.5711 (4)	0.9250 (2)	0.76324 (14)	0.0561 (6)
C5	0.3478 (4)	0.7912 (2)	0.72494 (13)	0.0505 (6)
C6	0.3109 (5)	0.7164 (2)	0.62499 (14)	0.0560 (7)
C7	0.3337 (5)	0.8703 (3)	0.88552 (16)	0.0631 (7)
C8	−0.0468 (5)	0.6251 (3)	0.80638 (19)	0.0638 (8)
C9	0.0397 (5)	0.4632 (2)	0.80549 (16)	0.0620 (7)
C10	0.2970 (8)	0.3200 (3)	0.9038 (2)	0.0878 (10)
H2	0.879 (6)	0.960 (3)	0.559 (2)	0.0930*
H3	0.927 (6)	1.086 (3)	0.7256 (19)	0.0930*
H6	0.165 (6)	0.628 (3)	0.600 (2)	0.0930*
H7	0.268 (6)	0.869 (3)	0.952 (2)	0.0930*
H8A	−0.177 (6)	0.619 (3)	0.745 (2)	0.0930*
H8B	−0.130 (6)	0.650 (3)	0.870 (2)	0.0930*
H9A	−0.135 (6)	0.374 (3)	0.8049 (19)	0.0930*
H9B	0.135 (6)	0.431 (3)	0.743 (2)	0.0930*
H10A	0.370 (7)	0.277 (4)	0.839 (3)	0.1160*
H10B	0.118 (7)	0.235 (4)	0.910 (2)	0.1160*
H10C	0.423 (7)	0.331 (4)	0.958 (3)	0.1160*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.1401 (18)	0.1222 (16)	0.0743 (12)	0.0128 (14)	0.0427 (13)	−0.0058 (11)
O2	0.1071 (14)	0.1233 (15)	0.0573 (10)	0.0054 (12)	−0.0080 (9)	−0.0277 (10)
O3	0.0989 (12)	0.0620 (9)	0.0612 (9)	0.0128 (8)	−0.0189 (8)	−0.0024 (6)
N1	0.0912 (15)	0.0837 (13)	0.0510 (10)	0.0264 (12)	0.0014 (11)	−0.0064 (10)
N2	0.0889 (14)	0.0504 (9)	0.0557 (10)	0.0103 (9)	−0.0057 (9)	−0.0131 (7)
N3	0.0608 (10)	0.0510 (8)	0.0480 (9)	0.0167 (7)	−0.0031 (7)	−0.0057 (7)
C1	0.0707 (14)	0.0606 (11)	0.0466 (11)	0.0226 (10)	0.0009 (10)	−0.0029 (9)
C2	0.0801 (16)	0.0619 (13)	0.0686 (14)	0.0130 (12)	0.0120 (12)	0.0053 (10)
C3	0.0793 (15)	0.0483 (11)	0.0729 (14)	0.0045 (10)	−0.0008 (12)	−0.0031 (10)
C4	0.0691 (13)	0.0432 (9)	0.0516 (11)	0.0166 (9)	−0.0080 (9)	−0.0067 (8)
C5	0.0549 (11)	0.0488 (10)	0.0470 (10)	0.0200 (8)	−0.0038 (8)	−0.0032 (8)
C6	0.0553 (12)	0.0558 (11)	0.0520 (11)	0.0168 (9)	−0.0093 (9)	−0.0077 (9)
C7	0.0826 (16)	0.0538 (11)	0.0495 (11)	0.0214 (11)	−0.0033 (10)	−0.0087 (9)
C8	0.0574 (13)	0.0701 (13)	0.0601 (13)	0.0167 (10)	0.0024 (10)	−0.0066 (10)
C9	0.0616 (13)	0.0582 (12)	0.0568 (12)	0.0032 (10)	−0.0045 (10)	−0.0047 (9)
C10	0.109 (2)	0.0633 (15)	0.0839 (18)	0.0089 (14)	−0.0182 (16)	0.0173 (13)

Geometric parameters (Å, º)

O1—N1	1.218 (3)	C4—C5	1.405 (3)
O2—N1	1.217 (3)	C5—C6	1.388 (3)
O3—C9	1.405 (3)	C8—C9	1.505 (3)
O3—C10	1.410 (3)	C2—H2	0.97 (3)
N1—C1	1.467 (3)	C3—H3	1.01 (3)
N2—C4	1.384 (3)	C6—H6	0.92 (3)
N2—C7	1.308 (3)	C7—H7	0.97 (3)
N3—C5	1.377 (2)	C8—H8A	0.98 (3)
N3—C7	1.361 (3)	C8—H8B	0.99 (3)
N3—C8	1.459 (3)	C9—H9A	1.01 (3)
C1—C2	1.398 (3)	C9—H9B	1.02 (3)
C1—C6	1.380 (3)	C10—H10A	1.02 (4)
C2—C3	1.375 (3)	C10—H10B	1.02 (3)
C3—C4	1.385 (3)	C10—H10C	0.89 (4)
O2···C9^i	3.335 (3)	C4···H8A^viii	3.05 (3)
O3···C7	3.321 (3)	C5···H9B	3.06 (3)
O3···N3	2.847 (2)	C5···H8A^viii	2.95 (3)
O1···H2	2.45 (3)	C6···H8A	2.99 (3)
O1···H9B^ii	2.77 (3)	C6···H9B	3.07 (3)
O1···H2^iii	2.82 (3)	C8···H6	3.03 (3)
O2···H6	2.43 (3)	C10···H3^x	3.08 (3)
O2···H9B^i	2.92 (3)	H2···O1	2.45 (3)
O2···H6^i	2.56 (3)	H2···O1^iii	2.82 (3)
O2···H8A^i	2.69 (3)	H2···H2^iii	2.14 (4)
O3···H10C^iv	2.66 (4)	H3···C10^xi	3.08 (3)
N2···N3	2.248 (2)	H6···O2	2.43 (3)
N2···C10^v	3.413 (4)	H6···C8	3.03 (3)
N2···C7^vi	3.395 (3)	H6···O2^i	2.56 (3)
N3···O3	2.847 (2)	H7···H8B	2.45 (4)
N3···C3^vii	3.441 (3)	H7···N2^vi	2.63 (3)
N3···N2	2.248 (2)	H8A···C4^vii	3.05 (3)
N2···H10A^v	2.94 (3)	H8A···C5^vii	2.95 (3)
N2···H7^vi	2.63 (3)	H8A···C6	2.99 (3)
C2···C6^viii	3.522 (4)	H8A···O2^i	2.69 (3)
C3···N3^viii	3.441 (3)	H8B···H7	2.45 (4)
C3···C5^viii	3.536 (3)	H9A···H10A^vii	2.46 (4)
C4···C8^viii	3.482 (3)	H9A···H10B	2.35 (4)
C5···C3^vii	3.536 (3)	H9B···C5	3.06 (3)
C6···C9	3.592 (3)	H9B···C6	3.07 (3)
C6···C2^vii	3.522 (4)	H9B···H10A	2.32 (4)
C7···C7^vi	3.586 (3)	H9B···O1^ii	2.77 (3)
C7···N2^vi	3.395 (3)	H9B···O2^i	2.92 (3)
C7···O3	3.321 (3)	H10A···N2^ix	2.94 (3)
C8···C4^vii	3.482 (3)	H10A···H9A^viii	2.46 (4)
C9···O2^i	3.335 (3)	H10A···H9B	2.32 (4)
C9···C6	3.592 (3)	H10B···H9A	2.35 (4)
C10···N2^ix	3.413 (4)	H10C···O3^iv	2.66 (4)
C9—O3—C10	111.92 (17)	C3—C2—H2	117.3 (16)
O1—N1—O2	122.9 (2)	C2—C3—H3	119.6 (15)
O1—N1—C1	118.5 (2)	C4—C3—H3	122.1 (15)
O2—N1—C1	118.6 (2)	C1—C6—H6	122.4 (17)
C4—N2—C7	104.01 (17)	C5—C6—H6	122.8 (17)
C5—N3—C7	105.68 (16)	N2—C7—H7	124.7 (16)
C5—N3—C8	127.05 (16)	N3—C7—H7	120.6 (16)
C7—N3—C8	127.16 (18)	N3—C8—H8A	107.5 (16)
N1—C1—C2	118.2 (2)	N3—C8—H8B	106.4 (16)
N1—C1—C6	117.88 (18)	C9—C8—H8A	108.1 (15)
C2—C1—C6	123.94 (19)	C9—C8—H8B	108.4 (15)
C1—C2—C3	119.9 (2)	H8A—C8—H8B	114 (2)
C2—C3—C4	118.3 (2)	O3—C9—H9A	109.7 (15)
N2—C4—C3	129.77 (18)	O3—C9—H9B	109.8 (16)
N2—C4—C5	110.04 (16)	C8—C9—H9A	110.0 (16)
C3—C4—C5	120.20 (18)	C8—C9—H9B	113.0 (15)
N3—C5—C4	105.54 (15)	H9A—C9—H9B	106 (2)
N3—C5—C6	131.64 (17)	O3—C10—H10A	109 (2)
C4—C5—C6	122.82 (17)	O3—C10—H10B	111 (2)
C1—C6—C5	114.78 (18)	O3—C10—H10C	110 (2)
N2—C7—N3	114.74 (19)	H10A—C10—H10B	105 (3)
N3—C8—C9	112.40 (19)	H10A—C10—H10C	113 (3)
O3—C9—C8	108.13 (17)	H10B—C10—H10C	110 (3)
C1—C2—H2	122.7 (16)
C10—O3—C9—C8	173.9 (2)	C5—N3—C8—C9	73.6 (3)
O1—N1—C1—C6	−177.4 (2)	C2—C1—C6—C5	−0.5 (3)
O2—N1—C1—C2	−179.6 (2)	N1—C1—C2—C3	−178.7 (2)
O1—N1—C1—C2	1.5 (3)	N1—C1—C6—C5	178.36 (19)
O2—N1—C1—C6	1.5 (3)	C6—C1—C2—C3	0.2 (4)
C7—N2—C4—C3	−179.8 (2)	C1—C2—C3—C4	0.5 (4)
C4—N2—C7—N3	0.3 (3)	C2—C3—C4—C5	−0.8 (3)
C7—N2—C4—C5	−0.5 (2)	C2—C3—C4—N2	178.5 (2)
C7—N3—C5—C6	179.1 (2)	C3—C4—C5—C6	0.5 (3)
C7—N3—C8—C9	−101.9 (2)	C3—C4—C5—N3	179.86 (18)
C5—N3—C7—N2	−0.1 (3)	N2—C4—C5—C6	−178.92 (18)
C8—N3—C5—C6	2.7 (3)	N2—C4—C5—N3	0.4 (2)
C7—N3—C5—C4	−0.2 (2)	N3—C5—C6—C1	−179.01 (19)
C8—N3—C5—C4	−176.54 (18)	C4—C5—C6—C1	0.2 (3)
C8—N3—C7—N2	176.3 (2)	N3—C8—C9—O3	61.2 (2)

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