Crystal structure of 5-chloro-1,3-bis-[2-(2-oxo-1,3-oxazolidin-3-yl)eth-yl]-1H-benz-imidazol-2(3H)-one.

In the title compound, C17H19ClN4O5, the benzimidazole fused-ring system is essentially planar, the maximum deviation from the mean plane being 0.06 (1) Å. Both oxazolidine rings are nearly planar, the maximum deviations from the mean planes are 0.071 (13) and 0.070 (10) Å. The dihedral angle between the mean planes of the oxazolidine rings is 69.9 (7)°. The benzimidazole mean plane makes the dihedral angles of 43.9 (6) and 45.6 (6)° with the two oxazolidine rings. In the crystal, the mol-ecules are linked together by weak C-H⋯O hydrogen bonds building zigzag tapes running along the c axis. The Cl atom is split over two positions with an occupancy ratio of 0.567 (7):0.433 (7). This means that the reaction yields two isomers, A and B; the A component has the Cl-atom substituent in the 5-position of the benzimidazolone ring and the B component has the Cl atom in the 6-position. The two isomers form the disordered co-crystal, with a nearly half Cl atom in each of them, as indicated by the occupancy ratio. The crystal structure was refined as an inversion twin.

Related literature

For biological properties of benzimidazol-2-one derivatives, see: Gribkoff et al. (1994 ▸); Olesen et al. (1994 ▸); Soderlind et al. (1999 ▸). For anti­bacterial activity oxazolidin-2-ones, see: Diekema & Jones (2000 ▸); Mukhtar & Wright (2005 ▸). For asymmetric reactions of oxazolidin-2-ones, see: Evans et al. (1993 ▸); Matsunaga et al. (2005 ▸). For oxazolidin-2-one derivatives, see: Ouzidan et al. (2011 ▸); Dardouri et al. (2011 ▸).

Experimental

Crystal data

C17H19ClN4O5

M = 394.81

Orthorhombic,

a = 14.053 (8) Å

b = 13.438 (6) Å

c = 9.733 (4) Å

V = 1838.1 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 296 K

0.35 × 0.31 × 0.26 mm

Data collection

Bruker X8 APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.504, T max = 0.748

9588 measured reflections

3701 independent reflections

1697 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.150

S = 1.01

3701 reflections

255 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.16 e Å−3

Absolute structure: Refined as an inversion twin

Absolute structure parameter: 0.5 (5)

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT-Plus (Bruker, 2009 ▸); data reduction: SAINT-Plus ; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 (Burnett & Johnson, 1996 ▸) and ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸) and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015016102/xu5863sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015016102/xu5863Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015016102/xu5863Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015016102/xu5863fig1.tif

Mol­ecular plot the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.

Click here for additional data file.

c . DOI: 10.1107/S2056989015016102/xu5863fig2.tif

Inter­molecular inter­actions in the title compound building a zigzag tape along c axis. Hydrogen bonds are shown as dashed lines.

CCDC reference: 1421051

Additional supporting information: crystallographic information; 3D view; checkCIF report

C17H19ClN4O5	Dx = 1.423 Mg m−3
Mr = 394.81	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 3701 reflections
a = 14.053 (8) Å	θ = 1.5–26.4°
b = 13.438 (6) Å	µ = 0.25 mm−1
c = 9.733 (4) Å	T = 296 K
V = 1838.1 (15) Å3	Block, colourless
Z = 4	0.35 × 0.31 × 0.26 mm
F(000) = 820

Bruker X8 APEX diffractometer	3701 independent reflections
Radiation source: fine-focus sealed tube	1697 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
φ and ω scans	θmax = 26.4°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→17
Tmin = 0.504, Tmax = 0.748	k = −16→16
9588 measured reflections	l = −12→12

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.057	w = 1/[σ2(Fo2) + (0.0473P)2 + 0.3226P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.150	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.21 e Å−3
3701 reflections	Δρmin = −0.16 e Å−3
255 parameters	Absolute structure: Refined as an inversion twin.
4 restraints	Absolute structure parameter: 0.5 (5)

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

Refinement. Refined as a 2-component inversion twin.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.5061 (11)	0.6238 (11)	0.3946 (17)	0.141 (6)
H1A	0.5660	0.5943	0.3660	0.169*
H1B	0.5119	0.6955	0.3879	0.169*
C2	0.4284 (10)	0.5885 (9)	0.3051 (13)	0.094 (4)
H2A	0.3888	0.6431	0.2737	0.113*
H2B	0.4527	0.5523	0.2264	0.113*
C3	0.4066 (8)	0.5371 (8)	0.5275 (13)	0.060 (3)
C4	0.2918 (6)	0.4698 (6)	0.3603 (12)	0.068 (3)
H4A	0.2585	0.5066	0.2894	0.082*
H4B	0.2501	0.4650	0.4395	0.082*
C5	0.3133 (7)	0.3677 (7)	0.3089 (10)	0.074 (3)
H5A	0.2552	0.3394	0.2721	0.089*
H5B	0.3582	0.3733	0.2336	0.089*
C6	0.4456 (8)	0.2814 (7)	0.4386 (11)	0.058 (3)
C7	0.5213 (9)	0.3189 (9)	0.3704 (15)	0.093 (4)
H7	0.5100	0.3570	0.2923	0.111*
C8	0.6121 (8)	0.3041 (8)	0.4091 (11)	0.093 (3)
H8	0.6648	0.3351	0.3704	0.112*	0.567 (7)
C9	0.6151 (7)	0.2357 (7)	0.5151 (15)	0.085 (4)
H9	0.6762	0.2161	0.5395	0.102*	0.433 (7)
C10	0.5401 (8)	0.1888 (8)	0.5959 (13)	0.087 (4)
H10	0.5521	0.1462	0.6692	0.104*
C11	0.4446 (10)	0.2151 (7)	0.5506 (11)	0.067 (3)
C12	0.2912 (5)	0.2497 (9)	0.5031 (13)	0.0513 (14)
C13	0.3124 (7)	0.1304 (6)	0.6914 (9)	0.071 (3)
H13A	0.2538	0.1570	0.7293	0.085*
H13B	0.3582	0.1240	0.7654	0.085*
C14	0.2935 (7)	0.0280 (6)	0.6264 (11)	0.067 (3)
H14A	0.2558	−0.0113	0.6898	0.080*
H14B	0.2560	0.0373	0.5437	0.080*
C15	0.4330 (8)	−0.0839 (8)	0.6883 (11)	0.068 (3)
H15A	0.3959	−0.1385	0.7256	0.081*
H15B	0.4552	−0.0423	0.7632	0.081*
C16	0.5157 (7)	−0.1221 (8)	0.6022 (10)	0.075 (3)
H16A	0.5743	−0.0876	0.6247	0.090*
H16B	0.5248	−0.1931	0.6146	0.090*
C17	0.4082 (9)	−0.0368 (8)	0.4637 (11)	0.066 (3)
N1	0.3770 (6)	0.5234 (5)	0.3986 (8)	0.052 (2)
N2	0.3510 (7)	0.3007 (6)	0.4064 (9)	0.064 (2)
N3	0.3503 (6)	0.1993 (5)	0.5834 (8)	0.0473 (19)
N4	0.3790 (6)	−0.0276 (6)	0.5914 (9)	0.059 (2)
O1	0.4858 (6)	0.5965 (7)	0.5304 (9)	0.094 (3)
O2	0.3747 (6)	0.4989 (7)	0.6326 (8)	0.094 (3)
O3	0.2045 (3)	0.2489 (6)	0.4997 (11)	0.0705 (11)
O4	0.3742 (6)	−0.0045 (6)	0.3617 (8)	0.096 (3)
O5	0.4846 (6)	−0.0991 (6)	0.4629 (8)	0.087 (3)
Cl1A	0.7305 (5)	0.2867 (5)	0.4090 (11)	0.103 (4)	0.433 (7)
Cl1B	0.7313 (5)	0.2114 (5)	0.5813 (11)	0.140 (4)	0.567 (7)

	U11	U22	U33	U12	U13	U23
C1	0.139 (13)	0.160 (14)	0.123 (13)	−0.094 (11)	0.019 (12)	0.004 (12)
C2	0.131 (13)	0.087 (10)	0.064 (8)	−0.026 (9)	0.012 (9)	0.007 (7)
C3	0.053 (8)	0.066 (7)	0.060 (7)	−0.007 (5)	−0.007 (6)	−0.006 (6)
C4	0.067 (9)	0.056 (7)	0.082 (8)	−0.004 (5)	−0.033 (6)	0.012 (6)
C5	0.104 (10)	0.066 (8)	0.053 (6)	−0.031 (6)	−0.025 (7)	0.003 (6)
C6	0.040 (7)	0.060 (6)	0.074 (8)	−0.013 (6)	0.008 (6)	−0.028 (6)
C7	0.070 (8)	0.105 (9)	0.103 (8)	−0.019 (7)	0.012 (7)	−0.040 (7)
C8	0.076 (8)	0.106 (9)	0.097 (7)	−0.015 (6)	0.012 (6)	−0.010 (6)
C9	0.047 (5)	0.071 (8)	0.137 (11)	0.024 (5)	−0.028 (8)	−0.047 (7)
C10	0.099 (10)	0.077 (7)	0.084 (7)	0.048 (8)	−0.036 (7)	−0.051 (6)
C11	0.099 (11)	0.044 (5)	0.058 (7)	0.009 (6)	−0.012 (7)	−0.020 (6)
C12	0.070 (4)	0.041 (3)	0.043 (3)	−0.013 (7)	0.002 (7)	−0.003 (2)
C13	0.120 (11)	0.045 (6)	0.047 (5)	0.003 (6)	0.021 (6)	0.008 (5)
C14	0.102 (10)	0.046 (6)	0.052 (6)	0.018 (6)	0.018 (6)	0.007 (5)
C15	0.083 (9)	0.063 (8)	0.056 (6)	0.014 (6)	−0.006 (6)	0.013 (6)
C16	0.089 (8)	0.082 (7)	0.055 (6)	0.023 (6)	−0.013 (6)	−0.007 (6)
C17	0.079 (10)	0.080 (8)	0.038 (6)	0.000 (7)	0.006 (7)	−0.003 (6)
N1	0.075 (6)	0.037 (5)	0.042 (4)	−0.019 (4)	0.000 (5)	−0.004 (4)
N2	0.090 (7)	0.048 (5)	0.055 (5)	−0.005 (5)	0.005 (6)	−0.007 (4)
N3	0.054 (5)	0.041 (5)	0.047 (4)	0.003 (4)	0.001 (4)	0.010 (4)
N4	0.079 (7)	0.059 (6)	0.040 (4)	0.004 (5)	0.015 (5)	0.013 (4)
O1	0.096 (7)	0.120 (7)	0.064 (5)	−0.036 (6)	−0.001 (5)	−0.019 (5)
O2	0.097 (7)	0.135 (7)	0.051 (5)	−0.013 (5)	0.005 (4)	0.012 (5)
O3	0.055 (3)	0.068 (2)	0.090 (3)	−0.008 (5)	0.002 (7)	−0.0005 (19)
O4	0.098 (7)	0.151 (8)	0.038 (4)	0.031 (5)	0.003 (4)	0.019 (5)
O5	0.082 (6)	0.113 (7)	0.066 (5)	0.037 (5)	0.015 (5)	−0.008 (5)
Cl1A	0.067 (6)	0.075 (5)	0.166 (8)	−0.006 (4)	0.006 (5)	0.010 (5)
Cl1B	0.071 (5)	0.123 (5)	0.226 (9)	0.038 (4)	−0.040 (5)	0.020 (6)

C1—O1	1.401 (15)	C9—Cl1A	2.042 (15)
C1—C2	1.475 (17)	C9—H9	0.9300
C1—H1A	0.9700	C10—C11	1.456 (15)
C1—H1B	0.9700	C10—H10	0.9300
C2—N1	1.454 (13)	C11—N3	1.379 (14)
C2—H2A	0.9700	C12—O3	1.219 (6)
C2—H2B	0.9700	C12—N3	1.326 (12)
C3—O2	1.230 (14)	C12—N2	1.436 (13)
C3—N1	1.334 (14)	C13—N3	1.499 (11)
C3—O1	1.369 (12)	C13—C14	1.538 (12)
C4—N1	1.447 (11)	C13—H13A	0.9700
C4—C5	1.491 (12)	C13—H13B	0.9700
C4—H4A	0.9700	C14—N4	1.455 (11)
C4—H4B	0.9700	C14—H14A	0.9700
C5—N2	1.411 (12)	C14—H14B	0.9700
C5—H5A	0.9700	C15—N4	1.428 (12)
C5—H5B	0.9700	C15—C16	1.522 (13)
C6—C7	1.352 (16)	C15—H15A	0.9700
C6—N2	1.391 (13)	C15—H15B	0.9700
C6—C11	1.408 (8)	C16—O5	1.458 (11)
C7—C8	1.345 (10)	C16—H16A	0.9700
C7—H7	0.9300	C16—H16B	0.9700
C8—C9	1.383 (11)	C17—O4	1.183 (14)
C8—Cl1A	1.680 (13)	C17—N4	1.315 (14)
C8—H8	0.9300	C17—O5	1.362 (13)
C9—C10	1.458 (10)	Cl1A—Cl1B	1.959 (6)
C9—Cl1B	1.786 (10)
O1—C1—C2	108.8 (11)	N3—C11—C6	106.6 (12)
O1—C1—H1A	109.9	N3—C11—C10	141.1 (11)
C2—C1—H1A	109.9	C6—C11—C10	112.2 (14)
O1—C1—H1B	109.9	O3—C12—N3	129.7 (12)
C2—C1—H1B	109.9	O3—C12—N2	124.8 (12)
H1A—C1—H1B	108.3	N3—C12—N2	105.3 (5)
N1—C2—C1	101.1 (10)	N3—C13—C14	109.0 (7)
N1—C2—H2A	111.6	N3—C13—H13A	109.9
C1—C2—H2A	111.6	C14—C13—H13A	109.9
N1—C2—H2B	111.6	N3—C13—H13B	109.9
C1—C2—H2B	111.6	C14—C13—H13B	109.9
H2A—C2—H2B	109.4	H13A—C13—H13B	108.3
O2—C3—N1	127.6 (10)	N4—C14—C13	114.4 (8)
O2—C3—O1	121.5 (11)	N4—C14—H14A	108.7
N1—C3—O1	110.7 (11)	C13—C14—H14A	108.7
N1—C4—C5	112.2 (8)	N4—C14—H14B	108.7
N1—C4—H4A	109.2	C13—C14—H14B	108.7
C5—C4—H4A	109.2	H14A—C14—H14B	107.6
N1—C4—H4B	109.2	N4—C15—C16	102.8 (8)
C5—C4—H4B	109.2	N4—C15—H15A	111.2
H4A—C4—H4B	107.9	C16—C15—H15A	111.2
N2—C5—C4	115.9 (8)	N4—C15—H15B	111.2
N2—C5—H5A	108.3	C16—C15—H15B	111.2
C4—C5—H5A	108.3	H15A—C15—H15B	109.1
N2—C5—H5B	108.3	O5—C16—C15	102.2 (8)
C4—C5—H5B	108.3	O5—C16—H16A	111.3
H5A—C5—H5B	107.4	C15—C16—H16A	111.3
C7—C6—N2	124.9 (12)	O5—C16—H16B	111.3
C7—C6—C11	128.7 (15)	C15—C16—H16B	111.3
N2—C6—C11	106.4 (12)	H16A—C16—H16B	109.2
C8—C7—C6	123.6 (14)	O4—C17—N4	129.3 (12)
C8—C7—H7	118.2	O4—C17—O5	122.5 (11)
C6—C7—H7	118.2	N4—C17—O5	108.0 (10)
C7—C8—C9	109.6 (11)	C3—N1—C4	124.7 (9)
C7—C8—Cl1A	163.7 (10)	C3—N1—C2	110.5 (9)
C9—C8—Cl1A	83.0 (9)	C4—N1—C2	123.4 (9)
C7—C8—H8	125.2	C6—N2—C5	129.0 (10)
C9—C8—H8	125.2	C6—N2—C12	108.8 (9)
Cl1A—C8—H8	43.4	C5—N2—C12	121.7 (10)
C8—C9—C10	131.9 (10)	C12—N3—C11	112.8 (8)
C8—C9—Cl1B	114.8 (10)	C12—N3—C13	120.4 (9)
C10—C9—Cl1B	112.8 (9)	C11—N3—C13	126.7 (9)
C8—C9—Cl1A	54.8 (8)	C17—N4—C15	114.1 (10)
C10—C9—Cl1A	172.8 (7)	C17—N4—C14	121.8 (10)
Cl1B—C9—Cl1A	61.2 (4)	C15—N4—C14	123.8 (8)
C8—C9—H9	114.0	C3—O1—C1	107.4 (10)
C10—C9—H9	114.0	C17—O5—C16	111.2 (8)
Cl1B—C9—H9	8.4	C8—Cl1A—Cl1B	94.4 (5)
Cl1A—C9—H9	59.3	C8—Cl1A—C9	42.2 (4)
C11—C10—C9	113.4 (10)	Cl1B—Cl1A—C9	53.0 (4)
C11—C10—H10	123.3	C9—Cl1B—Cl1A	65.9 (6)
C9—C10—H10	123.3

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O2i	0.97	2.42	3.247 (13)	143
C14—H14A···O4ii	0.97	2.48	3.315 (13)	144

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C4H4AO2i	0.97	2.42	3.247(13)	143
C14H14AO4ii	0.97	2.48	3.315(13)	144

Symmetry codes: (i) ; (ii) .