3-[2-(2-Amino-1H-benzo[d]imidazol-1-yl)eth­yl]-1,3-oxazolidin-2-one

In the title compound, C₁₂H₁₄N₄O₂, the benzimidazole ring is almost planar (r.m.s. deviation = 0.03 Å), with the fused ring system slightly folded at the shared atoms, with a dihedral angle of 3.4 (1)°. The oxazolidinone ring displays a twisted conformation on the –CH₂–CH₂– bond and its mean plane makes a dihedral angle of 57.4 (1)° with the benzimidazole ring mean plane. In the crystal, mol­ecules are linked by N—H...O and N—H...N hydrogen bonds, forming chains propagating along the a-axis direction. The chains are linked by C—H...O and C—H...N hydrogen bonds, forming a three-dimensional structure, which is reinforced by C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.035
• wR factor = 0.100
• Data-to-parameter ratio = 20.4

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack parameter is too small
           From the CIF: _refine_ls_abs_structure_Flack   -0.300
           From the CIF: _refine_ls_abs_structure_Flack_su    0.300

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      0.300 Report
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           7 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

3-[2-(2-Amino-1H-benzo[d]imidazol-1-yl)ethyl]-1,3-oxazolidin-2-one

Crystal data

C12H14N4O2	Dx = 1.389 Mg m^−3
Mr = 246.27	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 3320 reflections
a = 9.0504 (2) Å	θ = 2.7–29.6°
b = 9.0612 (1) Å	µ = 0.10 mm^−1
c = 14.3565 (2) Å	T = 296 K
V = 1177.34 (3) Å^3	Block, colourless
Z = 4	0.44 × 0.34 × 0.26 mm
F(000) = 520

Data collection

Bruker X8 APEX diffractometer	3320 independent reflections
Radiation source: fine-focus sealed tube	3097 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
φ and ω scans	θmax = 29.6°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −12→12
Tmin = 0.663, Tmax = 0.746	k = −12→12
46121 measured reflections	l = −19→19

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)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.100	w = 1/[σ^2(Fo^2) + (0.0582P)^2 + 0.1462P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
3320 reflections	Δρmax = 0.20 e Å^−3
163 parameters	Δρmin = −0.24 e Å^−3
1 restraint	Absolute structure: Flack x determined using 1380 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.3 (3)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.98692 (19)	0.55021 (18)	0.54222 (14)	0.0305 (3)
C2	1.1216 (2)	0.5197 (2)	0.49961 (18)	0.0408 (4)
H2	1.2096	0.5567	0.5237	0.049*
C3	1.1210 (3)	0.4324 (2)	0.42002 (19)	0.0480 (5)
H3	1.2102	0.4110	0.3908	0.058*
C4	0.9909 (3)	0.3764 (2)	0.38293 (17)	0.0479 (5)
H4	0.9947	0.3177	0.3298	0.057*
C5	0.8550 (2)	0.4067 (2)	0.42404 (15)	0.0396 (4)
H5	0.7674	0.3698	0.3995	0.047*
C6	0.85612 (19)	0.49410 (19)	0.50313 (13)	0.0292 (3)
C7	0.80874 (18)	0.63783 (18)	0.62457 (12)	0.0276 (3)
C8	0.58530 (19)	0.5271 (2)	0.54381 (13)	0.0318 (4)
H8A	0.5635	0.5317	0.4777	0.038*
H8B	0.5305	0.6055	0.5743	0.038*
C9	0.5335 (2)	0.3792 (2)	0.58184 (13)	0.0346 (4)
H9A	0.4274	0.3718	0.5737	0.042*
H9B	0.5788	0.3009	0.5457	0.042*
C10	0.6839 (4)	0.2609 (4)	0.7117 (2)	0.0633 (8)
H10A	0.7806	0.2972	0.6936	0.076*
H10B	0.6712	0.1612	0.6884	0.076*
C11	0.6626 (4)	0.2679 (3)	0.8156 (2)	0.0661 (8)
H11A	0.6234	0.1753	0.8389	0.079*
H11B	0.7557	0.2879	0.8466	0.079*
C12	0.5022 (2)	0.4301 (2)	0.74885 (15)	0.0357 (4)
N1	0.95466 (16)	0.63860 (17)	0.61871 (12)	0.0322 (3)
N2	0.74285 (16)	0.55200 (16)	0.55759 (10)	0.0285 (3)
N3	0.73039 (18)	0.71167 (19)	0.69026 (12)	0.0362 (3)
H3A	0.7756	0.7632	0.7317	0.043*
H3B	0.6355	0.7069	0.6905	0.043*
N4	0.56840 (19)	0.35663 (18)	0.67963 (12)	0.0337 (3)
O1	0.5596 (3)	0.3860 (2)	0.83151 (12)	0.0560 (5)
O2	0.4053 (2)	0.52092 (19)	0.74365 (15)	0.0548 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0284 (8)	0.0282 (7)	0.0350 (9)	−0.0007 (6)	0.0017 (7)	0.0036 (7)
C2	0.0310 (8)	0.0388 (9)	0.0526 (12)	0.0001 (7)	0.0087 (9)	0.0003 (9)
C3	0.0476 (12)	0.0429 (10)	0.0534 (13)	0.0076 (9)	0.0210 (10)	0.0027 (10)
C4	0.0621 (14)	0.0433 (10)	0.0383 (11)	0.0036 (10)	0.0122 (10)	−0.0042 (9)
C5	0.0464 (11)	0.0388 (9)	0.0335 (9)	−0.0026 (8)	0.0000 (8)	−0.0018 (8)
C6	0.0301 (7)	0.0289 (7)	0.0286 (8)	−0.0002 (6)	0.0030 (7)	0.0041 (6)
C7	0.0263 (7)	0.0289 (7)	0.0276 (7)	−0.0008 (6)	−0.0032 (6)	0.0024 (6)
C8	0.0257 (7)	0.0387 (8)	0.0312 (9)	−0.0022 (6)	−0.0056 (7)	0.0034 (7)
C9	0.0317 (8)	0.0397 (9)	0.0325 (9)	−0.0070 (7)	−0.0013 (7)	−0.0038 (7)
C10	0.0683 (17)	0.0687 (17)	0.0529 (13)	0.0356 (14)	−0.0008 (13)	0.0052 (12)
C11	0.093 (2)	0.0564 (15)	0.0491 (14)	0.0210 (15)	−0.0150 (15)	0.0098 (12)
C12	0.0363 (9)	0.0335 (8)	0.0373 (9)	−0.0036 (7)	0.0085 (8)	−0.0001 (8)
N1	0.0249 (6)	0.0339 (7)	0.0377 (8)	−0.0011 (6)	−0.0009 (6)	−0.0027 (6)
N2	0.0240 (6)	0.0331 (7)	0.0282 (7)	−0.0026 (5)	−0.0008 (5)	−0.0002 (5)
N3	0.0268 (7)	0.0458 (8)	0.0362 (8)	0.0023 (6)	−0.0011 (6)	−0.0089 (7)
N4	0.0347 (8)	0.0340 (7)	0.0325 (8)	0.0049 (6)	0.0030 (6)	0.0008 (6)
O1	0.0754 (12)	0.0597 (10)	0.0330 (7)	0.0104 (9)	0.0072 (8)	0.0016 (7)
O2	0.0462 (8)	0.0498 (9)	0.0685 (12)	0.0139 (7)	0.0149 (9)	−0.0051 (8)

Geometric parameters (Å, º)

C1—N1	1.390 (3)	C8—H8A	0.9700
C1—C2	1.392 (3)	C8—H8B	0.9700
C1—C6	1.405 (2)	C9—N4	1.453 (3)
C2—C3	1.390 (4)	C9—H9A	0.9700
C2—H2	0.9300	C9—H9B	0.9700
C3—C4	1.388 (4)	C10—N4	1.434 (3)
C3—H3	0.9300	C10—C11	1.506 (4)
C4—C5	1.392 (3)	C10—H10A	0.9700
C4—H4	0.9300	C10—H10B	0.9700
C5—C6	1.384 (3)	C11—O1	1.437 (3)
C5—H5	0.9300	C11—H11A	0.9700
C6—N2	1.392 (2)	C11—H11B	0.9700
C7—N1	1.323 (2)	C12—O2	1.206 (3)
C7—N3	1.356 (2)	C12—N4	1.337 (3)
C7—N2	1.373 (2)	C12—O1	1.356 (3)
C8—N2	1.457 (2)	N3—H3A	0.8600
C8—C9	1.522 (3)	N3—H3B	0.8600
N1—C1—C2	130.21 (18)	N4—C9—H9B	108.8
N1—C1—C6	110.30 (15)	C8—C9—H9B	108.8
C2—C1—C6	119.38 (18)	H9A—C9—H9B	107.7
C3—C2—C1	118.1 (2)	N4—C10—C11	101.5 (2)
C3—C2—H2	121.0	N4—C10—H10A	111.5
C1—C2—H2	121.0	C11—C10—H10A	111.5
C4—C3—C2	121.8 (2)	N4—C10—H10B	111.5
C4—C3—H3	119.1	C11—C10—H10B	111.5
C2—C3—H3	119.1	H10A—C10—H10B	109.3
C3—C4—C5	121.0 (2)	O1—C11—C10	105.8 (2)
C3—C4—H4	119.5	O1—C11—H11A	110.6
C5—C4—H4	119.5	C10—C11—H11A	110.6
C6—C5—C4	117.0 (2)	O1—C11—H11B	110.6
C6—C5—H5	121.5	C10—C11—H11B	110.6
C4—C5—H5	121.5	H11A—C11—H11B	108.7
C5—C6—N2	132.14 (17)	O2—C12—N4	128.3 (2)
C5—C6—C1	122.73 (17)	O2—C12—O1	122.3 (2)
N2—C6—C1	105.05 (16)	N4—C12—O1	109.41 (17)
N1—C7—N3	124.29 (17)	C7—N1—C1	104.88 (15)
N1—C7—N2	113.07 (16)	C7—N2—C6	106.68 (14)
N3—C7—N2	122.63 (15)	C7—N2—C8	127.43 (15)
N2—C8—C9	112.90 (15)	C6—N2—C8	125.88 (15)
N2—C8—H8A	109.0	C7—N3—H3A	120.0
C9—C8—H8A	109.0	C7—N3—H3B	120.0
N2—C8—H8B	109.0	H3A—N3—H3B	120.0
C9—C8—H8B	109.0	C12—N4—C10	112.89 (19)
H8A—C8—H8B	107.8	C12—N4—C9	123.40 (17)
N4—C9—C8	113.80 (16)	C10—N4—C9	123.59 (19)
N4—C9—H9A	108.8	C12—O1—C11	109.20 (18)
C8—C9—H9A	108.8
N1—C1—C2—C3	−176.61 (19)	N1—C7—N2—C8	−179.77 (16)
C6—C1—C2—C3	−0.8 (3)	N3—C7—N2—C8	1.1 (3)
C1—C2—C3—C4	0.1 (3)	C5—C6—N2—C7	−176.61 (19)
C2—C3—C4—C5	0.5 (4)	C1—C6—N2—C7	0.17 (18)
C3—C4—C5—C6	−0.2 (3)	C5—C6—N2—C8	2.3 (3)
C4—C5—C6—N2	175.75 (19)	C1—C6—N2—C8	179.11 (16)
C4—C5—C6—C1	−0.6 (3)	C9—C8—N2—C7	−101.4 (2)
N1—C1—C6—C5	177.68 (17)	C9—C8—N2—C6	79.8 (2)
C2—C1—C6—C5	1.1 (3)	O2—C12—N4—C10	177.6 (3)
N1—C1—C6—N2	0.51 (19)	O1—C12—N4—C10	−3.2 (3)
C2—C1—C6—N2	−176.04 (17)	O2—C12—N4—C9	1.5 (3)
N2—C8—C9—N4	55.4 (2)	O1—C12—N4—C9	−179.31 (18)
N4—C10—C11—O1	−10.9 (4)	C11—C10—N4—C12	8.9 (3)
N3—C7—N1—C1	−179.78 (16)	C11—C10—N4—C9	−175.0 (2)
N2—C7—N1—C1	1.1 (2)	C8—C9—N4—C12	70.4 (2)
C2—C1—N1—C7	175.1 (2)	C8—C9—N4—C10	−105.2 (3)
C6—C1—N1—C7	−1.0 (2)	O2—C12—O1—C11	174.7 (2)
N1—C7—N2—C6	−0.9 (2)	N4—C12—O1—C11	−4.5 (3)
N3—C7—N2—C6	−179.95 (16)	C10—C11—O1—C12	9.9 (4)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2^i	0.86	2.29	2.994 (2)	140
N3—H3B···N1^ii	0.86	2.39	3.020 (2)	131
C8—H8A···O1^iii	0.97	2.49	3.410 (3)	158
C8—H8B···N1^ii	0.97	2.50	3.425 (2)	159
C9—H9A···Cg1^iv	0.97	2.80	3.571 (2)	137
C11—H11B···Cg1^v	0.97	2.80	3.730 (3)	161

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