Crystal structure of (E)-N'-benzyl-idene-1-methyl-4-nitro-1H-pyrrole-2-carbohydrazide.

In the title compound, C13H12N4O3, the dihedral angle between the planes of the pyrrole and benzene rings is 7.47 (1)°. In the crystal, mol-ecules are arranged in sheets lying parallel to (101). Neighbouring sheets are linked by N-H⋯O hydrogen bonds, weak π-π [centroid-centroid distance between the pyrrole rings = 3.765 (11) Å] and C-H⋯π inter-actions, forming a three-dimensional structure.

Related literature

For applications and structures of aroylhydrazones, see: Krishnamoorthy et al. (2012 ▶); Raja et al. (2012 ▶); Wang et al. (2014 ▶). For similar structures, see: Wang et al. (2011 ▶, 2014 ▶). For π–π inter­actions, see: Janiak (2000 ▶).

Experimental

Crystal data

C13H12N4O3

M = 272.27

Monoclinic,

a = 13.030 (3) Å

b = 11.900 (3) Å

c = 8.331 (2) Å

β = 95.409 (3)°

V = 1285.92 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.32 × 0.20 × 0.17 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.968, T max = 0.983

6283 measured reflections

2248 independent reflections

1382 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.135

S = 1.03

2248 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and DIAMOND (Brandenburg, 2005 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814018054/bt6990sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814018054/bt6990Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814018054/bt6990Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814018054/bt6990fig1.tif

The mol­ecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radius.

Click here for additional data file.

. DOI: 10.1107/S1600536814018054/bt6990fig2.tif

Mol­ecules of the title compound forming planes parallel to the (101) plane.

Click here for additional data file.

. DOI: 10.1107/S1600536814018054/bt6990fig3.tif

The inter­molecular N–H⋯O hydrogen bonds (black dotted lines), π⋯π and C–H⋯π inter­actions (pink dotted lines) between adjacent sheets (H atoms not involved in hydrogen bonds have been omitted for clarity, all distances in Å).

Click here for additional data file.

b . DOI: 10.1107/S1600536814018054/bt6990fig4.tif

Packing of the title compound viewed along the b axis.

CCDC reference: 1018158

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

C13H12N4O3	F(000) = 568
Mr = 272.27	Dx = 1.406 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1529 reflections
a = 13.030 (3) Å	θ = 2.3–24.0°
b = 11.900 (3) Å	µ = 0.10 mm−1
c = 8.331 (2) Å	T = 298 K
β = 95.409 (3)°	Block, yellow
V = 1285.92 (17) Å3	0.32 × 0.20 × 0.17 mm
Z = 4

Bruker SMART 1000 CCD diffractometer	2248 independent reflections
Radiation source: fine-focus sealed tube	1382 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
phi and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→15
Tmin = 0.968, Tmax = 0.983	k = −14→14
6283 measured reflections	l = −9→9

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0571P)2 + 0.2921P] where P = (Fo2 + 2Fc2)/3
2248 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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. 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 > σ(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
N1	0.80415 (15)	0.34342 (17)	0.4275 (2)	0.0409 (5)
N2	0.74919 (15)	0.27603 (17)	0.5233 (2)	0.0435 (6)
H2	0.7314	0.3006	0.6138	0.052*
N3	0.64881 (15)	−0.00154 (17)	0.5892 (2)	0.0436 (6)
N4	0.45223 (18)	0.0771 (3)	0.8358 (3)	0.0618 (7)
O1	0.75036 (14)	0.12934 (15)	0.3497 (2)	0.0540 (5)
O2	0.41349 (15)	−0.0109 (2)	0.8783 (2)	0.0804 (7)
O3	0.42286 (18)	0.1703 (2)	0.8735 (3)	0.0916 (8)
C1	0.72375 (18)	0.1713 (2)	0.4734 (3)	0.0397 (6)
C2	0.65549 (18)	0.1145 (2)	0.5783 (3)	0.0386 (6)
C3	0.58369 (18)	0.1601 (2)	0.6690 (3)	0.0441 (7)
H3	0.5704	0.2361	0.6829	0.053*
C4	0.53470 (19)	0.0704 (2)	0.7359 (3)	0.0469 (7)
C5	0.57607 (19)	−0.0277 (2)	0.6867 (3)	0.0502 (7)
H5	0.5572	−0.0998	0.7156	0.060*
C6	0.7129 (2)	−0.0846 (2)	0.5155 (3)	0.0560 (8)
H6A	0.6865	−0.1586	0.5319	0.084*
H6B	0.7825	−0.0796	0.5644	0.084*
H6C	0.7117	−0.0700	0.4020	0.084*
C7	0.81171 (19)	0.4454 (2)	0.4711 (3)	0.0419 (6)
H7	0.7786	0.4697	0.5589	0.050*
C8	0.87158 (18)	0.5250 (2)	0.3853 (3)	0.0388 (6)
C9	0.93840 (19)	0.4903 (2)	0.2762 (3)	0.0467 (7)
H9	0.9426	0.4143	0.2512	0.056*
C10	0.9988 (2)	0.5662 (2)	0.2040 (3)	0.0530 (8)
H10	1.0445	0.5413	0.1324	0.064*
C11	0.9919 (2)	0.6776 (3)	0.2370 (3)	0.0604 (8)
H11	1.0330	0.7290	0.1885	0.072*
C12	0.9246 (3)	0.7139 (2)	0.3416 (4)	0.0724 (10)
H12	0.9186	0.7903	0.3620	0.087*
C13	0.8655 (2)	0.6380 (2)	0.4170 (3)	0.0587 (8)
H13	0.8210	0.6635	0.4901	0.070*

	U11	U22	U33	U12	U13	U23
N1	0.0444 (12)	0.0449 (13)	0.0346 (12)	−0.0062 (10)	0.0097 (10)	0.0028 (10)
N2	0.0533 (13)	0.0436 (12)	0.0362 (13)	−0.0105 (10)	0.0172 (10)	−0.0027 (10)
N3	0.0437 (13)	0.0442 (13)	0.0428 (13)	−0.0056 (10)	0.0024 (10)	0.0019 (11)
N4	0.0421 (14)	0.096 (2)	0.0474 (15)	−0.0117 (15)	0.0069 (12)	0.0073 (16)
O1	0.0735 (13)	0.0526 (11)	0.0388 (11)	−0.0083 (10)	0.0211 (10)	−0.0081 (9)
O2	0.0547 (13)	0.1207 (19)	0.0668 (15)	−0.0377 (13)	0.0107 (11)	0.0153 (14)
O3	0.0764 (17)	0.112 (2)	0.0932 (19)	0.0082 (15)	0.0433 (14)	−0.0026 (17)
C1	0.0425 (15)	0.0449 (16)	0.0319 (15)	−0.0037 (12)	0.0039 (12)	0.0031 (13)
C2	0.0400 (14)	0.0439 (15)	0.0316 (14)	−0.0057 (12)	0.0009 (11)	0.0038 (12)
C3	0.0436 (15)	0.0507 (16)	0.0385 (16)	−0.0035 (13)	0.0065 (13)	0.0029 (13)
C4	0.0354 (14)	0.0679 (19)	0.0379 (16)	−0.0091 (14)	0.0054 (12)	0.0040 (14)
C5	0.0473 (17)	0.0566 (18)	0.0455 (17)	−0.0171 (14)	−0.0013 (14)	0.0101 (14)
C6	0.0604 (19)	0.0455 (16)	0.061 (2)	0.0004 (14)	0.0017 (15)	−0.0036 (14)
C7	0.0439 (15)	0.0466 (16)	0.0367 (15)	0.0009 (13)	0.0115 (12)	−0.0018 (13)
C8	0.0417 (14)	0.0402 (15)	0.0343 (15)	−0.0041 (11)	0.0023 (12)	0.0002 (12)
C9	0.0474 (16)	0.0388 (15)	0.0552 (17)	0.0036 (12)	0.0116 (14)	0.0038 (13)
C10	0.0493 (16)	0.0574 (19)	0.0547 (19)	−0.0070 (14)	0.0177 (14)	0.0038 (15)
C11	0.075 (2)	0.0553 (19)	0.0521 (19)	−0.0224 (16)	0.0116 (16)	0.0043 (15)
C12	0.110 (3)	0.0413 (17)	0.069 (2)	−0.0147 (18)	0.025 (2)	−0.0071 (16)
C13	0.078 (2)	0.0486 (18)	0.0523 (19)	−0.0055 (15)	0.0238 (16)	−0.0101 (15)

N1—C7	1.268 (3)	C6—H6A	0.9600
N1—N2	1.379 (3)	C6—H6B	0.9600
N2—C1	1.346 (3)	C6—H6C	0.9600
N2—H2	0.8600	C7—C8	1.456 (3)
N3—C5	1.342 (3)	C7—H7	0.9300
N3—C2	1.386 (3)	C8—C13	1.374 (3)
N3—C6	1.466 (3)	C8—C9	1.380 (3)
N4—O3	1.224 (3)	C9—C10	1.374 (3)
N4—O2	1.230 (3)	C9—H9	0.9300
N4—C4	1.422 (3)	C10—C11	1.359 (4)
O1—C1	1.224 (3)	C10—H10	0.9300
C1—C2	1.469 (3)	C11—C12	1.363 (4)
C2—C3	1.369 (3)	C11—H11	0.9300
C3—C4	1.387 (3)	C12—C13	1.376 (4)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.365 (4)	C13—H13	0.9300
C5—H5	0.9300
C7—N1—N2	114.9 (2)	N3—C6—H6B	109.5
C1—N2—N1	119.1 (2)	H6A—C6—H6B	109.5
C1—N2—H2	120.5	N3—C6—H6C	109.5
N1—N2—H2	120.5	H6A—C6—H6C	109.5
C5—N3—C2	108.8 (2)	H6B—C6—H6C	109.5
C5—N3—C6	124.1 (2)	N1—C7—C8	120.8 (2)
C2—N3—C6	127.0 (2)	N1—C7—H7	119.6
O3—N4—O2	123.5 (3)	C8—C7—H7	119.6
O3—N4—C4	118.2 (3)	C13—C8—C9	118.1 (2)
O2—N4—C4	118.3 (3)	C13—C8—C7	119.9 (2)
O1—C1—N2	123.8 (2)	C9—C8—C7	121.9 (2)
O1—C1—C2	123.3 (2)	C10—C9—C8	121.0 (2)
N2—C1—C2	112.8 (2)	C10—C9—H9	119.5
C3—C2—N3	108.0 (2)	C8—C9—H9	119.5
C3—C2—C1	129.0 (2)	C11—C10—C9	120.1 (3)
N3—C2—C1	122.8 (2)	C11—C10—H10	119.9
C2—C3—C4	106.3 (2)	C9—C10—H10	119.9
C2—C3—H3	126.8	C10—C11—C12	119.8 (3)
C4—C3—H3	126.8	C10—C11—H11	120.1
C5—C4—C3	109.1 (2)	C12—C11—H11	120.1
C5—C4—N4	124.4 (3)	C11—C12—C13	120.4 (3)
C3—C4—N4	126.4 (3)	C11—C12—H12	119.8
N3—C5—C4	107.8 (2)	C13—C12—H12	119.8
N3—C5—H5	126.1	C8—C13—C12	120.6 (3)
C4—C5—H5	126.1	C8—C13—H13	119.7
N3—C6—H6A	109.5	C12—C13—H13	119.7
C7—N1—N2—C1	170.0 (2)	O3—N4—C4—C3	−3.2 (4)
N1—N2—C1—O1	3.3 (4)	O2—N4—C4—C3	176.1 (3)
N1—N2—C1—C2	−173.4 (2)	C2—N3—C5—C4	1.1 (3)
C5—N3—C2—C3	−1.1 (3)	C6—N3—C5—C4	178.1 (2)
C6—N3—C2—C3	−178.0 (2)	C3—C4—C5—N3	−0.7 (3)
C5—N3—C2—C1	−176.4 (2)	N4—C4—C5—N3	177.4 (2)
C6—N3—C2—C1	6.7 (4)	N2—N1—C7—C8	177.2 (2)
O1—C1—C2—C3	−146.8 (3)	N1—C7—C8—C13	169.5 (3)
N2—C1—C2—C3	29.9 (4)	N1—C7—C8—C9	−13.1 (4)
O1—C1—C2—N3	27.4 (4)	C13—C8—C9—C10	1.4 (4)
N2—C1—C2—N3	−155.9 (2)	C7—C8—C9—C10	−176.0 (2)
N3—C2—C3—C4	0.7 (3)	C8—C9—C10—C11	−1.3 (4)
C1—C2—C3—C4	175.6 (2)	C9—C10—C11—C12	−0.2 (5)
C2—C3—C4—C5	0.0 (3)	C10—C11—C12—C13	1.7 (5)
C2—C3—C4—N4	−178.1 (2)	C9—C8—C13—C12	0.0 (4)
O3—N4—C4—C5	179.0 (3)	C7—C8—C13—C12	177.5 (3)
O2—N4—C4—C5	−1.7 (4)	C11—C12—C13—C8	−1.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.86	2.13	2.942 (2)	158
C6—H6B···Cgi	0.96	2.70	3.590 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.86	2.13	2.942 (2)	158
C6—H6B⋯Cg i	0.96	2.70	3.590 (3)	154

Symmetry code: (i) .