Crystal structure of ethyl 2-(1H-benzimidazol-2-yl)-2-[2-(4-nitro-phen-yl)hydrazinyl-idene]acetate.

The title compound, C17H15N5O4, was obtained via the condensation of 3-eth-oxy-2-[2-(4-nitro-phen-yl)hydrazono]-3-oxo-propanoic acid with 1,2-di-amino-benzene. In the mol-ecule, the dihedral angles between the acetate group and the two aromatic subunits (benzimidazole and nitro-phenyl-hydrazone) are 7.35 (9) and 18.23 (9)°, respectively. Intra-molecular N-H⋯O and N-H⋯N contacts occur. In the crystal, C-H⋯O and N-H⋯O hydrogen bonds link the mol-ecules into chains along the b-axis direction.

Related literature

For the pharmacological activity of benzimidazole derivatives, see: Luo et al. (2011 ▸); Ouattara et al. (2011 ▸); Bhrigu et al. (2012 ▸); Singh et al. (2012 ▸); Parajuli et al. (2014 ▸). For their agrochemical activity, see: Attrassi et al. (2007 ▸).

Experimental

Crystal data

C17H15N5O4

M = 353.34

Monoclinic,

a = 12.877 (5) Å

b = 5.874 (5) Å

c = 21.988 (5) Å

β = 99.060 (5)°

V = 1642.4 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.33 × 0.17 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer

24995 measured reflections

3362 independent reflections

2562 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.108

S = 1.03

3362 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.17 e Å−3

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: SHELXL97 (Sheldrick,2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015004818/im2461sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015004818/im2461Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015004818/im2461Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015004818/im2461fig1.tif

Mol­ecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.

Click here for additional data file.

b . DOI: 10.1107/S2056989015004818/im2461fig2.tif

Partial packing view showing the C—H⋯O and N—H⋯O inter­actions (dashed lines) and the formation of a chain parallel to the b axis. H atoms not involved in hydrogen bonding have been omitted for clarity.

CCDC reference: 1052904

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

C17H15N5O4	F(000) = 736
Mr = 353.34	Dx = 1.429 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3362 reflections
a = 12.877 (5) Å	θ = 2.7–26.4°
b = 5.874 (5) Å	µ = 0.11 mm−1
c = 21.988 (5) Å	T = 293 K
β = 99.060 (5)°	Platelet, colourless
V = 1642.4 (16) Å3	0.33 × 0.17 × 0.04 mm
Z = 4

Bruker APEXII CCD diffractometer	2562 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
Graphite monochromator	θmax = 26.4°, θmin = 2.7°
ω and φ scans	h = −16→16
24995 measured reflections	k = −7→7
3362 independent reflections	l = −27→27

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0471P)2 + 0.5028P] where P = (Fo2 + 2Fc2)/3
3362 reflections	(Δ/σ)max < 0.001
236 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) 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.

	x	y	z	Uiso*/Ueq
C1	0.24083 (11)	0.7913 (3)	0.32924 (7)	0.0367 (3)
C12	0.49273 (11)	0.6017 (3)	0.39833 (6)	0.0349 (3)
C13	0.46733 (12)	0.3904 (3)	0.42102 (7)	0.0405 (4)
H13	0.3980	0.3398	0.4147	0.049*
C5	0.25493 (11)	0.9962 (3)	0.29411 (7)	0.0357 (3)
C15	0.64834 (12)	0.3339 (3)	0.46186 (7)	0.0415 (4)
C2	0.13384 (12)	0.6936 (3)	0.32829 (7)	0.0413 (4)
C17	0.59698 (12)	0.6755 (3)	0.40730 (7)	0.0406 (4)
H17	0.6138	0.8155	0.3917	0.049*
C6	0.32726 (11)	1.2789 (3)	0.25402 (7)	0.0365 (3)
C11	0.39466 (12)	1.4456 (3)	0.23679 (7)	0.0410 (4)
H11	0.4662	1.4438	0.2521	0.049*
C16	0.67524 (12)	0.5414 (3)	0.43928 (7)	0.0439 (4)
H16	0.7448	0.5900	0.4455	0.053*
C8	0.17657 (12)	1.4543 (3)	0.18916 (8)	0.0460 (4)
H8	0.1052	1.4564	0.1733	0.055*
C9	0.24422 (13)	1.6167 (3)	0.17267 (8)	0.0470 (4)
H9	0.2180	1.7311	0.1453	0.056*
C14	0.54567 (13)	0.2574 (3)	0.45284 (7)	0.0437 (4)
H14	0.5295	0.1165	0.4682	0.052*
C10	0.35198 (12)	1.6127 (3)	0.19643 (7)	0.0441 (4)
H10	0.3955	1.7253	0.1847	0.053*
C7	0.21950 (11)	1.2872 (3)	0.23044 (7)	0.0378 (3)
C3	0.03236 (14)	0.4189 (4)	0.37222 (10)	0.0645 (5)
H3A	0.0032	0.3445	0.3339	0.077*
H3B	−0.0167	0.5349	0.3811	0.077*
N1	0.34778 (9)	1.0947 (2)	0.29374 (6)	0.0382 (3)
N2	0.17568 (9)	1.1066 (2)	0.25700 (6)	0.0401 (3)
H2	0.1102	1.0698	0.2513	0.048*
N3	0.31612 (9)	0.6757 (2)	0.36227 (6)	0.0384 (3)
N4	0.41544 (9)	0.7421 (2)	0.36668 (6)	0.0390 (3)
H4	0.4316	0.8680	0.3505	0.047*
N5	0.73044 (13)	0.1896 (3)	0.49538 (7)	0.0567 (4)
O1	0.82217 (12)	0.2456 (3)	0.49629 (8)	0.0857 (5)
O2	0.70291 (13)	0.0185 (2)	0.52145 (7)	0.0771 (4)
O3	0.13339 (9)	0.5214 (2)	0.36682 (6)	0.0566 (3)
O4	0.05567 (8)	0.7645 (2)	0.29566 (6)	0.0548 (3)
C4	0.04983 (17)	0.2514 (4)	0.42261 (11)	0.0837 (7)
H4A	0.0745	0.3282	0.4607	0.126*
H4B	0.1014	0.1423	0.4144	0.126*
H4C	−0.0150	0.1746	0.4256	0.126*

	U11	U22	U33	U12	U13	U23
C1	0.0289 (7)	0.0419 (8)	0.0390 (8)	0.0026 (6)	0.0040 (6)	−0.0048 (6)
C12	0.0317 (7)	0.0409 (8)	0.0317 (7)	0.0023 (6)	0.0040 (6)	−0.0034 (6)
C13	0.0342 (8)	0.0451 (9)	0.0424 (8)	−0.0027 (7)	0.0063 (7)	−0.0026 (7)
C5	0.0284 (7)	0.0394 (8)	0.0388 (8)	0.0026 (6)	0.0036 (6)	−0.0068 (6)
C15	0.0431 (9)	0.0444 (9)	0.0354 (8)	0.0112 (7)	0.0012 (6)	−0.0017 (7)
C2	0.0333 (8)	0.0440 (8)	0.0465 (9)	0.0006 (7)	0.0063 (7)	−0.0017 (7)
C17	0.0349 (8)	0.0401 (8)	0.0462 (9)	−0.0013 (6)	0.0042 (7)	0.0037 (7)
C6	0.0311 (7)	0.0399 (8)	0.0382 (8)	0.0027 (6)	0.0048 (6)	−0.0064 (6)
C11	0.0305 (7)	0.0482 (9)	0.0444 (9)	−0.0024 (6)	0.0059 (6)	−0.0075 (7)
C16	0.0307 (8)	0.0520 (10)	0.0478 (9)	0.0002 (7)	0.0024 (7)	−0.0031 (8)
C8	0.0317 (8)	0.0497 (9)	0.0546 (10)	0.0042 (7)	0.0009 (7)	0.0016 (8)
C9	0.0449 (9)	0.0457 (9)	0.0504 (9)	0.0047 (7)	0.0082 (7)	0.0033 (8)
C14	0.0509 (10)	0.0395 (8)	0.0416 (8)	0.0002 (7)	0.0098 (7)	0.0019 (7)
C10	0.0420 (9)	0.0452 (9)	0.0467 (9)	−0.0055 (7)	0.0122 (7)	−0.0042 (7)
C7	0.0297 (7)	0.0396 (8)	0.0439 (8)	0.0008 (6)	0.0052 (6)	−0.0045 (7)
C3	0.0377 (9)	0.0708 (12)	0.0829 (14)	−0.0125 (9)	0.0033 (9)	0.0184 (11)
N1	0.0289 (6)	0.0420 (7)	0.0430 (7)	0.0009 (5)	0.0036 (5)	−0.0044 (6)
N2	0.0249 (6)	0.0435 (7)	0.0505 (8)	0.0004 (5)	0.0017 (5)	0.0006 (6)
N3	0.0297 (6)	0.0451 (7)	0.0402 (7)	0.0003 (5)	0.0046 (5)	−0.0049 (6)
N4	0.0279 (6)	0.0435 (7)	0.0443 (7)	−0.0005 (5)	0.0015 (5)	0.0026 (6)
N5	0.0581 (10)	0.0579 (10)	0.0501 (9)	0.0171 (8)	−0.0038 (7)	−0.0030 (8)
O1	0.0495 (8)	0.0996 (12)	0.1017 (12)	0.0226 (8)	−0.0076 (8)	0.0158 (10)
O2	0.0933 (11)	0.0556 (8)	0.0748 (10)	0.0155 (8)	−0.0109 (8)	0.0150 (7)
O3	0.0330 (6)	0.0639 (8)	0.0703 (8)	−0.0079 (5)	0.0002 (5)	0.0183 (6)
O4	0.0278 (6)	0.0640 (8)	0.0704 (8)	0.0009 (5)	0.0006 (5)	0.0136 (6)
C4	0.0629 (13)	0.0951 (17)	0.0888 (16)	−0.0217 (12)	−0.0014 (12)	0.0320 (14)

C1—N3	1.3064 (19)	C16—H16	0.9300
C1—C5	1.457 (2)	C8—C9	1.378 (2)
C1—C2	1.490 (2)	C8—C7	1.391 (2)
C12—N4	1.3921 (19)	C8—H8	0.9300
C12—C17	1.395 (2)	C9—C10	1.404 (2)
C12—C13	1.396 (2)	C9—H9	0.9300
C13—C14	1.377 (2)	C14—H14	0.9300
C13—H13	0.9300	C10—H10	0.9300
C5—N1	1.3295 (19)	C7—N2	1.374 (2)
C5—N2	1.3659 (19)	C3—O3	1.455 (2)
C15—C16	1.381 (2)	C3—C4	1.472 (3)
C15—C14	1.381 (2)	C3—H3A	0.9700
C15—N5	1.461 (2)	C3—H3B	0.9700
C2—O4	1.2140 (18)	N2—H2	0.8600
C2—O3	1.320 (2)	N3—N4	1.3259 (17)
C17—C16	1.381 (2)	N4—H4	0.8600
C17—H17	0.9300	N5—O1	1.223 (2)
C6—N1	1.389 (2)	N5—O2	1.236 (2)
C6—C11	1.400 (2)	C4—H4A	0.9600
C6—C7	1.404 (2)	C4—H4B	0.9600
C11—C10	1.378 (2)	C4—H4C	0.9600
C11—H11	0.9300
N3—C1—C5	125.50 (13)	C10—C9—H9	119.4
N3—C1—C2	114.28 (14)	C13—C14—C15	119.79 (15)
C5—C1—C2	120.20 (13)	C13—C14—H14	120.1
N4—C12—C17	118.87 (14)	C15—C14—H14	120.1
N4—C12—C13	121.10 (13)	C11—C10—C9	121.48 (15)
C17—C12—C13	120.03 (14)	C11—C10—H10	119.3
C14—C13—C12	119.47 (15)	C9—C10—H10	119.3
C14—C13—H13	120.3	N2—C7—C8	132.42 (14)
C12—C13—H13	120.3	N2—C7—C6	105.33 (13)
N1—C5—N2	112.18 (14)	C8—C7—C6	122.25 (14)
N1—C5—C1	123.37 (13)	O3—C3—C4	107.77 (15)
N2—C5—C1	124.43 (13)	O3—C3—H3A	110.2
C16—C15—C14	121.63 (14)	C4—C3—H3A	110.2
C16—C15—N5	119.41 (15)	O3—C3—H3B	110.2
C14—C15—N5	118.96 (16)	C4—C3—H3B	110.2
O4—C2—O3	123.72 (14)	H3A—C3—H3B	108.5
O4—C2—C1	123.71 (15)	C5—N1—C6	105.10 (12)
O3—C2—C1	112.57 (13)	C5—N2—C7	107.60 (12)
C16—C17—C12	120.24 (15)	C5—N2—H2	126.2
C16—C17—H17	119.9	C7—N2—H2	126.2
C12—C17—H17	119.9	C1—N3—N4	120.69 (14)
N1—C6—C11	130.57 (14)	N3—N4—C12	117.87 (13)
N1—C6—C7	109.78 (13)	N3—N4—H4	121.1
C11—C6—C7	119.65 (14)	C12—N4—H4	121.1
C10—C11—C6	118.11 (14)	O1—N5—O2	123.90 (16)
C10—C11—H11	120.9	O1—N5—C15	118.19 (17)
C6—C11—H11	120.9	O2—N5—C15	117.91 (17)
C15—C16—C17	118.83 (15)	C2—O3—C3	117.63 (13)
C15—C16—H16	120.6	C3—C4—H4A	109.5
C17—C16—H16	120.6	C3—C4—H4B	109.5
C9—C8—C7	117.22 (15)	H4A—C4—H4B	109.5
C9—C8—H8	121.4	C3—C4—H4C	109.5
C7—C8—H8	121.4	H4A—C4—H4C	109.5
C8—C9—C10	121.29 (16)	H4B—C4—H4C	109.5
C8—C9—H9	119.4

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4i	0.86	2.50	3.161 (3)	134
C8—H8···O4i	0.93	2.54	3.258 (3)	134
N2—H2···O4	0.86	2.21	2.750 (3)	121
N4—H4···N1	0.86	2.02	2.679 (3)	133

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N2H2O4i	0.86	2.50	3.161(3)	134
C8H8O4i	0.93	2.54	3.258(3)	134
N2H2O4	0.86	2.21	2.750(3)	121
N4H4N1	0.86	2.02	2.679(3)	133

Symmetry code: (i) .