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

In the title compound, C13H11ClN4O3, the phenyl and pyrrolyl ring are linked by an ac-yl-hydrazone (R 2C=N-N-CO-R) group, forming a slightly bent mol-ecule: the dihedral angle subtended by the the phenyl and pyrrolyl rings is 8.46 (12)°. In the crystal, the three-dimensional supra-molecular structure is assembled by N-H⋯O hydrogen bonding. Mol-ecular sheets are formed parallel to (101) in a herringbone arrangement by weak van der Waals inter-actions; weak π-π [centroid-centroid phen-yl-phenyl and pyrrol-yl-pyrrolyl distances of 3.7816 (3) and 3.8946 (2) Å, respectively] inter-actions occur between neighbouring sheets.

Related literature

For applications and structures of aroylhydrazones, see: Raja et al. (2012 ▶); Wang et al. (2014 ▶).

Experimental

Crystal data

C13H11ClN4O3

M = 306.71

Monoclinic,

a = 13.7649 (13) Å

b = 12.4993 (11) Å

c = 8.1263 (10) Å

β = 95.523 (1)°

V = 1391.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 298 K

0.30 × 0.20 × 0.16 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.918, T max = 0.955

6871 measured reflections

2452 independent reflections

1435 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.164

S = 1.00

2452 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.33 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: DIAMOND (Brandenburg, 1999 ▶) and SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and SHELXTL.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813034119/ff2124sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813034119/ff2124Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813034119/ff2124Isup3.cml

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

C13H11ClN4O3	F(000) = 632
Mr = 306.71	Dx = 1.464 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.7649 (13) Å	Cell parameters from 1539 reflections
b = 12.4993 (11) Å	θ = 3.0–25.2°
c = 8.1263 (10) Å	µ = 0.29 mm−1
β = 95.523 (1)°	T = 298 K
V = 1391.7 (2) Å3	Block, yellow
Z = 4	0.30 × 0.20 × 0.16 mm

Bruker SMART 1000 CCD diffractometer	2452 independent reflections
Radiation source: fine-focus sealed tube	1435 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.071
phi and ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −15→16
Tmin = 0.918, Tmax = 0.955	k = −14→14
6871 measured reflections	l = −6→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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0787P)2] where P = (Fo2 + 2Fc2)/3
2452 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.33 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
Cl1	0.29032 (9)	1.16858 (8)	1.00653 (18)	0.1044 (6)
N1	0.14340 (19)	0.51021 (19)	1.0868 (3)	0.0508 (7)
N2	−0.0430 (2)	0.5940 (3)	1.3388 (4)	0.0712 (9)
N3	0.24317 (19)	0.7725 (2)	1.0085 (3)	0.0512 (8)
H3	0.2231	0.7996	1.0964	0.061*
N4	0.30201 (18)	0.83156 (19)	0.9133 (3)	0.0470 (7)
O1	0.24317 (17)	0.62828 (16)	0.8366 (3)	0.0587 (7)
O2	−0.0656 (2)	0.6852 (3)	1.3780 (4)	0.1057 (12)
O3	−0.08399 (19)	0.5122 (3)	1.3789 (3)	0.0907 (9)
C1	0.2175 (2)	0.6716 (2)	0.9618 (4)	0.0465 (8)
C2	0.1506 (2)	0.6203 (2)	1.0708 (4)	0.0451 (8)
C3	0.0829 (2)	0.6674 (3)	1.1612 (4)	0.0514 (8)
H3A	0.0711	0.7403	1.1715	0.062*
C4	0.0352 (2)	0.5839 (3)	1.2344 (4)	0.0561 (9)
C5	0.0737 (2)	0.4884 (3)	1.1897 (4)	0.0573 (9)
H5	0.0554	0.4209	1.2235	0.069*
C6	0.2046 (3)	0.4285 (3)	1.0169 (5)	0.0659 (10)
H6A	0.2708	0.4362	1.0642	0.099*
H6B	0.2017	0.4376	0.8992	0.099*
H6C	0.1810	0.3586	1.0416	0.099*
C7	0.3117 (2)	0.9297 (2)	0.9548 (4)	0.0483 (8)
H7	0.2764	0.9569	1.0373	0.058*
C8	0.3779 (2)	1.0000 (2)	0.8743 (4)	0.0467 (8)
C9	0.3778 (2)	1.1102 (2)	0.8944 (4)	0.0571 (9)
C10	0.4438 (3)	1.1761 (3)	0.8256 (5)	0.0698 (11)
H10	0.4413	1.2498	0.8406	0.084*
C11	0.5133 (3)	1.1319 (3)	0.7348 (5)	0.0698 (11)
H11	0.5587	1.1756	0.6900	0.084*
C12	0.5154 (3)	1.0231 (3)	0.7108 (5)	0.0659 (10)
H12	0.5620	0.9933	0.6491	0.079*
C13	0.4481 (2)	0.9577 (3)	0.7784 (4)	0.0568 (9)
H13	0.4497	0.8843	0.7598	0.068*

	U11	U22	U33	U12	U13	U23
Cl1	0.1002 (9)	0.0517 (6)	0.1730 (14)	0.0028 (6)	0.0731 (9)	−0.0179 (7)
N1	0.0553 (16)	0.0427 (14)	0.0560 (18)	−0.0065 (13)	0.0130 (13)	0.0045 (13)
N2	0.057 (2)	0.102 (3)	0.057 (2)	−0.019 (2)	0.0189 (16)	0.0023 (19)
N3	0.0646 (18)	0.0459 (15)	0.0477 (17)	−0.0109 (13)	0.0286 (14)	−0.0042 (12)
N4	0.0549 (16)	0.0436 (15)	0.0455 (16)	−0.0057 (13)	0.0199 (13)	0.0025 (11)
O1	0.0821 (17)	0.0499 (12)	0.0490 (14)	−0.0105 (12)	0.0310 (12)	−0.0064 (11)
O2	0.088 (2)	0.121 (3)	0.117 (3)	−0.010 (2)	0.056 (2)	−0.027 (2)
O3	0.0637 (17)	0.134 (3)	0.077 (2)	−0.0337 (18)	0.0193 (14)	0.0198 (18)
C1	0.053 (2)	0.0444 (17)	0.045 (2)	−0.0027 (15)	0.0197 (15)	0.0023 (14)
C2	0.0476 (18)	0.0425 (16)	0.047 (2)	−0.0063 (14)	0.0123 (15)	−0.0010 (14)
C3	0.0496 (19)	0.0530 (18)	0.054 (2)	−0.0032 (16)	0.0153 (16)	−0.0007 (16)
C4	0.0516 (19)	0.069 (2)	0.050 (2)	−0.0095 (18)	0.0160 (16)	0.0016 (17)
C5	0.059 (2)	0.059 (2)	0.055 (2)	−0.0168 (18)	0.0113 (17)	0.0151 (17)
C6	0.075 (3)	0.0447 (18)	0.079 (3)	0.0036 (18)	0.014 (2)	0.0010 (18)
C7	0.0515 (19)	0.0442 (18)	0.053 (2)	−0.0001 (15)	0.0227 (16)	−0.0005 (15)
C8	0.0473 (18)	0.0431 (16)	0.052 (2)	−0.0039 (15)	0.0150 (15)	0.0006 (14)
C9	0.056 (2)	0.0442 (18)	0.074 (3)	−0.0032 (16)	0.0199 (18)	0.0008 (17)
C10	0.068 (2)	0.0459 (19)	0.098 (3)	−0.0110 (18)	0.021 (2)	0.0092 (19)
C11	0.061 (2)	0.076 (3)	0.074 (3)	−0.013 (2)	0.016 (2)	0.018 (2)
C12	0.063 (2)	0.075 (3)	0.064 (3)	−0.002 (2)	0.0284 (19)	0.003 (2)
C13	0.064 (2)	0.0502 (19)	0.059 (2)	−0.0029 (17)	0.0220 (18)	0.0008 (16)

Cl1—C9	1.739 (3)	C5—H5	0.9300
N1—C5	1.359 (4)	C6—H6A	0.9600
N1—C2	1.387 (4)	C6—H6B	0.9600
N1—C6	1.472 (4)	C6—H6C	0.9600
N2—O3	1.227 (4)	C7—C8	1.465 (4)
N2—O2	1.232 (4)	C7—H7	0.9300
N2—C4	1.439 (4)	C8—C9	1.387 (4)
N3—C1	1.354 (4)	C8—C13	1.402 (4)
N3—N4	1.386 (3)	C9—C10	1.383 (5)
N3—H3	0.8600	C10—C11	1.379 (5)
N4—C7	1.276 (4)	C10—H10	0.9300
O1—C1	1.234 (3)	C11—C12	1.374 (5)
C1—C2	1.483 (4)	C11—H11	0.9300
C2—C3	1.374 (4)	C12—C13	1.388 (4)
C3—C4	1.397 (4)	C12—H12	0.9300
C3—H3A	0.9300	C13—H13	0.9300
C4—C5	1.369 (5)
C5—N1—C2	108.5 (3)	N1—C6—H6B	109.5
C5—N1—C6	124.2 (3)	H6A—C6—H6B	109.5
C2—N1—C6	127.1 (2)	N1—C6—H6C	109.5
O3—N2—O2	124.7 (3)	H6A—C6—H6C	109.5
O3—N2—C4	118.2 (4)	H6B—C6—H6C	109.5
O2—N2—C4	117.1 (3)	N4—C7—C8	120.8 (3)
C1—N3—N4	119.4 (2)	N4—C7—H7	119.6
C1—N3—H3	120.3	C8—C7—H7	119.6
N4—N3—H3	120.3	C9—C8—C13	116.7 (3)
C7—N4—N3	114.6 (2)	C9—C8—C7	122.4 (3)
O1—C1—N3	123.5 (3)	C13—C8—C7	120.9 (3)
O1—C1—C2	123.1 (3)	C10—C9—C8	122.4 (3)
N3—C1—C2	113.3 (3)	C10—C9—Cl1	118.5 (3)
C3—C2—N1	108.5 (3)	C8—C9—Cl1	119.1 (2)
C3—C2—C1	128.8 (3)	C11—C10—C9	119.6 (3)
N1—C2—C1	122.6 (3)	C11—C10—H10	120.2
C2—C3—C4	106.1 (3)	C9—C10—H10	120.2
C2—C3—H3A	126.9	C12—C11—C10	119.8 (3)
C4—C3—H3A	126.9	C12—C11—H11	120.1
C5—C4—C3	109.2 (3)	C10—C11—H11	120.1
C5—C4—N2	124.3 (3)	C11—C12—C13	120.2 (3)
C3—C4—N2	126.4 (3)	C11—C12—H12	119.9
N1—C5—C4	107.6 (3)	C13—C12—H12	119.9
N1—C5—H5	126.2	C12—C13—C8	121.3 (3)
C4—C5—H5	126.2	C12—C13—H13	119.4
N1—C6—H6A	109.5	C8—C13—H13	119.4
C1—N3—N4—C7	171.3 (3)	C2—N1—C5—C4	1.7 (4)
N4—N3—C1—O1	−0.5 (5)	C6—N1—C5—C4	177.5 (3)
N4—N3—C1—C2	−177.2 (3)	C3—C4—C5—N1	−1.2 (4)
C5—N1—C2—C3	−1.6 (4)	N2—C4—C5—N1	178.0 (3)
C6—N1—C2—C3	−177.2 (3)	N3—N4—C7—C8	175.1 (3)
C5—N1—C2—C1	−177.7 (3)	N4—C7—C8—C9	168.3 (3)
C6—N1—C2—C1	6.7 (5)	N4—C7—C8—C13	−14.7 (5)
O1—C1—C2—C3	−147.4 (4)	C13—C8—C9—C10	−0.6 (6)
N3—C1—C2—C3	29.3 (5)	C7—C8—C9—C10	176.4 (4)
O1—C1—C2—N1	27.9 (5)	C13—C8—C9—Cl1	178.0 (3)
N3—C1—C2—N1	−155.5 (3)	C7—C8—C9—Cl1	−4.9 (5)
N1—C2—C3—C4	0.8 (4)	C8—C9—C10—C11	−0.7 (6)
C1—C2—C3—C4	176.6 (3)	Cl1—C9—C10—C11	−179.4 (3)
C2—C3—C4—C5	0.3 (4)	C9—C10—C11—C12	1.2 (6)
C2—C3—C4—N2	−178.9 (3)	C10—C11—C12—C13	−0.4 (6)
O3—N2—C4—C5	−6.7 (6)	C11—C12—C13—C8	−1.0 (6)
O2—N2—C4—C5	175.1 (4)	C9—C8—C13—C12	1.5 (5)
O3—N2—C4—C3	172.3 (3)	C7—C8—C13—C12	−175.6 (3)
O2—N2—C4—C3	−5.9 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1i	0.86	2.14	2.941 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1i	0.86	2.14	2.941 (3)	154

Symmetry code: (i) .