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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 1| January 2014| Page o99
https://doi.org/10.1107/S1600536813034119

(E)-N′-(2-Chloro­benzyl­­idene)-1-methyl-4-nitro-1H-pyrrole-2-carbohydrazide

Jinglin Wang,a* Rong He,a Zhijuan Xin,a Huiling Shena and Cairong Wanga

aDepartment of Chemistry, Changzhi University, Changzhi, Shanxi 046011, People's Republic of China
*Correspondence e-mail: jlwangczu@163.com

(Received 8 December 2013; accepted 18 December 2013; online 24 December 2013)

In the title compound, C13H11ClN4O3, the phenyl and pyrrolyl ring are linked by an ac­yl–hydrazone (R2C=N—N—CO—R) group, forming a slightly bent mol­ecule: the dihedral angle subtended by the the phenyl and pyrrolyl rings is 8.46 (12)°. In the crystal, the three-dimensional supra­molecular structure is assembled by N—H⋯O hydrogen bonding. Mol­ecular sheets are formed parallel to (101) in a herringbone arrangement by weak van der Waals inter­actions; weak π–π [centroid–centroid phen­yl–phenyl and pyrrol­yl–pyrrolyl distances of 3.7816 (3) and 3.8946 (2) Å, respectively] inter­actions occur between neighbouring sheets.

CCDC reference: 977773

Related literature

For applications and structures of aroylhydrazones, see: Raja et al. (2012[Raja, D. S., Bhuvanesh, N. S. P. & Natarajan, K. (2012). Dalton Trans. 41, 4365-4377.]); Wang et al. (2014[Wang, J., Zhao, Y. & Yang, B. (2014). Inorg. Chim. Acta, 409, 484-496.]).

[Scheme 1]

Experimental

Crystal data

  • C13H11ClN4O3

  • Mr = 306.71

  • Monoclinic, P 21 /c

  • 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[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.918, Tmax = 0.955

  • 6871 measured reflections

  • 2452 independent reflections

  • 1435 reflections with I > 2σ(I)

  • Rint = 0.071
Refinement

  • R[F2 > 2σ(F2)] = 0.061

  • wR(F2) = 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

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) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 1999[Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1999[Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and SHELXTL.

Supporting information

CCDC reference: 977773

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S1600536813034119/ff2124sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813034119/ff2124Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813034119/ff2124Isup3.cml

checkCIF report


Comment top

A great number of aroylhydrazones (AH) have triggered wide interest because of their diverse spectra of biological and pharmaceutical properties (Raja, et al., 2012). In our lab, the AH compound (E)-N'-(2-hydroxybenzylidene)-1-methyl-4-nitro-1H-pyrrole-2-carbohydrazide (L) and its transition metal complexes were obtained and characterized. The interaction of these compounds with CT-DNA and pBR322 DNA has been explored (Wang, et al., 2014). The present report is an extension of our earlier studies in this area.

In the title compound (Fig. 1), C13H11ClN4O3, the phenyl and pyrrolyl ring are linked by acyl-hydrazone (R2C=N–N–CO–R) to form a slightly bent molecule. The dihedral angle between the phenyl (C8—C13) and pyrrolyl rings (C2—C5, N1) is 8.46 (12)°.

As shown in Figure 2, the herringbone molecular sheet of the title compound is formed by weak van-der-Waals interactions along (101) plane.

The three-dimensional supramolecular structure (Fig. 3) is assembled by N3–H3···O1i hydrogen bonding (pink dotted lines) and weak Cg1···Cg1ii (Cg1 is the centroid of the phenyl ring) and Cg2···Cg2iii (Cg2 is the centroid of the pyrrolyl ring) interactions (black dotted lines) between the neighbouring molecular sheets [symmetry code: (i) x, 3/2 - y, 1/2 + z; (ii)1 - x, 2 - y, 2 – z; (iii) - x, 1 - y, 2 - z]. The data of hydrogen-bond geometry are given in Table 1.

Related literature top

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

Experimental top

Single crystals of the title compound were obtained accidentally in the attempted synthesis of a Ni complex. (E)-N'-(2-hydroxybenzylidene)-1-methyl-4-nitro-1H-pyrrole-2-carbohydrazide (L) was synthesized according to literature procedures (Wang et al., 2014). Sodium methoxide (250 µL, 3%, g/V) was added to solution of L (0.50 mmol, 0.144 g) in 15 ml MeOH and was heated to reflux. NiCl2·6H2O (0.50 mmol, 0.119 g) was then added to the refluxing mixture and further refluxed for 2 h. The reaction mixture was cooled and was allowed to stir at room temperature overnight. The mixture was filtered and washed with methanol. The L—Ni complex is not achieved as predicted. However, orange single crystals of the title compound suitable for X-ray analysis were obtained after several days from the mother liquor by slow evaporation.

Refinement top

H atoms attached to C atoms are placed in geometrically idealized position, with N–H=0.86 Å, C–H=0.93 and 0.96 Å, for CH and CH3 groups, respectively, and with Uiso(H) = k × Ueq(parent C-atom), where k = 1.5 for CH3 H-atoms and =1.2 for other H-atoms.

Structure description top

A great number of aroylhydrazones (AH) have triggered wide interest because of their diverse spectra of biological and pharmaceutical properties (Raja, et al., 2012). In our lab, the AH compound (E)-N'-(2-hydroxybenzylidene)-1-methyl-4-nitro-1H-pyrrole-2-carbohydrazide (L) and its transition metal complexes were obtained and characterized. The interaction of these compounds with CT-DNA and pBR322 DNA has been explored (Wang, et al., 2014). The present report is an extension of our earlier studies in this area.

In the title compound (Fig. 1), C13H11ClN4O3, the phenyl and pyrrolyl ring are linked by acyl-hydrazone (R2C=N–N–CO–R) to form a slightly bent molecule. The dihedral angle between the phenyl (C8—C13) and pyrrolyl rings (C2—C5, N1) is 8.46 (12)°.

As shown in Figure 2, the herringbone molecular sheet of the title compound is formed by weak van-der-Waals interactions along (101) plane.

The three-dimensional supramolecular structure (Fig. 3) is assembled by N3–H3···O1i hydrogen bonding (pink dotted lines) and weak Cg1···Cg1ii (Cg1 is the centroid of the phenyl ring) and Cg2···Cg2iii (Cg2 is the centroid of the pyrrolyl ring) interactions (black dotted lines) between the neighbouring molecular sheets [symmetry code: (i) x, 3/2 - y, 1/2 + z; (ii)1 - x, 2 - y, 2 – z; (iii) - x, 1 - y, 2 - z]. The data of hydrogen-bond geometry are given in Table 1.

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

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius.
[Figure 2] Fig. 2. The two-dimensional herringbone layer in the crystal structure of title compound.
[Figure 3] Fig. 3. Packing of the title compound viewed along the b axis. The three-dimensional supramolecular structure is assembled by N–H···O hydrogen bonding (pink dotted lines) and weak π···π interactions (black dotted lines) between the neighbouring molecular sheets (all distances in Å).
(E)-N'-(2-Chlorobenzylidene)-1-methyl-4-nitro-1H-pyrrole-2-carbohydrazide top
Crystal data top
C13H11ClN4O3F(000) = 632
Mr = 306.71Dx = 1.464 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.7649 (13) ÅCell parameters from 1539 reflections
b = 12.4993 (11) Åθ = 3.0–25.2°
c = 8.1263 (10) ŵ = 0.29 mm−1
β = 95.523 (1)°T = 298 K
V = 1391.7 (2) Å3Block, yellow
Z = 40.30 × 0.20 × 0.16 mm
Data collection top
Bruker SMART 1000 CCD
diffractometer		2452 independent reflections
Radiation source: fine-focus sealed tube1435 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.071
phi and ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −15→16
Tmin = 0.918, Tmax = 0.955k = −14→14
6871 measured reflectionsl = −6→9
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H-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 parametersΔρmax = 0.23 e Å−3
0 restraintsΔρmin = −0.33 e Å−3
Crystal data top
C13H11ClN4O3V = 1391.7 (2) Å3
Mr = 306.71Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.7649 (13) ŵ = 0.29 mm−1
b = 12.4993 (11) ÅT = 298 K
c = 8.1263 (10) Å0.30 × 0.20 × 0.16 mm
β = 95.523 (1)°
Data collection top
Bruker SMART 1000 CCD
diffractometer		2452 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		1435 reflections with I > 2σ(I)
Tmin = 0.918, Tmax = 0.955Rint = 0.071
6871 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0610 restraints
wR(F2) = 0.164H-atom parameters constrained
S = 1.00Δρmax = 0.23 e Å−3
2452 reflectionsΔρmin = −0.33 e Å−3
191 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.29032 (9)1.16858 (8)1.00653 (18)0.1044 (6)
N10.14340 (19)0.51021 (19)1.0868 (3)0.0508 (7)
N2−0.0430 (2)0.5940 (3)1.3388 (4)0.0712 (9)
N30.24317 (19)0.7725 (2)1.0085 (3)0.0512 (8)
H30.22310.79961.09640.061*
N40.30201 (18)0.83156 (19)0.9133 (3)0.0470 (7)
O10.24317 (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)
C10.2175 (2)0.6716 (2)0.9618 (4)0.0465 (8)
C20.1506 (2)0.6203 (2)1.0708 (4)0.0451 (8)
C30.0829 (2)0.6674 (3)1.1612 (4)0.0514 (8)
H3A0.07110.74031.17150.062*
C40.0352 (2)0.5839 (3)1.2344 (4)0.0561 (9)
C50.0737 (2)0.4884 (3)1.1897 (4)0.0573 (9)
H50.05540.42091.22350.069*
C60.2046 (3)0.4285 (3)1.0169 (5)0.0659 (10)
H6A0.27080.43621.06420.099*
H6B0.20170.43760.89920.099*
H6C0.18100.35861.04160.099*
C70.3117 (2)0.9297 (2)0.9548 (4)0.0483 (8)
H70.27640.95691.03730.058*
C80.3779 (2)1.0000 (2)0.8743 (4)0.0467 (8)
C90.3778 (2)1.1102 (2)0.8944 (4)0.0571 (9)
C100.4438 (3)1.1761 (3)0.8256 (5)0.0698 (11)
H100.44131.24980.84060.084*
C110.5133 (3)1.1319 (3)0.7348 (5)0.0698 (11)
H110.55871.17560.69000.084*
C120.5154 (3)1.0231 (3)0.7108 (5)0.0659 (10)
H120.56200.99330.64910.079*
C130.4481 (2)0.9577 (3)0.7784 (4)0.0568 (9)
H130.44970.88430.75980.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1002 (9)0.0517 (6)0.1730 (14)0.0028 (6)0.0731 (9)−0.0179 (7)
N10.0553 (16)0.0427 (14)0.0560 (18)−0.0065 (13)0.0130 (13)0.0045 (13)
N20.057 (2)0.102 (3)0.057 (2)−0.019 (2)0.0189 (16)0.0023 (19)
N30.0646 (18)0.0459 (15)0.0477 (17)−0.0109 (13)0.0286 (14)−0.0042 (12)
N40.0549 (16)0.0436 (15)0.0455 (16)−0.0057 (13)0.0199 (13)0.0025 (11)
O10.0821 (17)0.0499 (12)0.0490 (14)−0.0105 (12)0.0310 (12)−0.0064 (11)
O20.088 (2)0.121 (3)0.117 (3)−0.010 (2)0.056 (2)−0.027 (2)
O30.0637 (17)0.134 (3)0.077 (2)−0.0337 (18)0.0193 (14)0.0198 (18)
C10.053 (2)0.0444 (17)0.045 (2)−0.0027 (15)0.0197 (15)0.0023 (14)
C20.0476 (18)0.0425 (16)0.047 (2)−0.0063 (14)0.0123 (15)−0.0010 (14)
C30.0496 (19)0.0530 (18)0.054 (2)−0.0032 (16)0.0153 (16)−0.0007 (16)
C40.0516 (19)0.069 (2)0.050 (2)−0.0095 (18)0.0160 (16)0.0016 (17)
C50.059 (2)0.059 (2)0.055 (2)−0.0168 (18)0.0113 (17)0.0151 (17)
C60.075 (3)0.0447 (18)0.079 (3)0.0036 (18)0.014 (2)0.0010 (18)
C70.0515 (19)0.0442 (18)0.053 (2)−0.0001 (15)0.0227 (16)−0.0005 (15)
C80.0473 (18)0.0431 (16)0.052 (2)−0.0039 (15)0.0150 (15)0.0006 (14)
C90.056 (2)0.0442 (18)0.074 (3)−0.0032 (16)0.0199 (18)0.0008 (17)
C100.068 (2)0.0459 (19)0.098 (3)−0.0110 (18)0.021 (2)0.0092 (19)
C110.061 (2)0.076 (3)0.074 (3)−0.013 (2)0.016 (2)0.018 (2)
C120.063 (2)0.075 (3)0.064 (3)−0.002 (2)0.0284 (19)0.003 (2)
C130.064 (2)0.0502 (19)0.059 (2)−0.0029 (17)0.0220 (18)0.0008 (16)
Geometric parameters (Å, º) top
Cl1—C91.739 (3)C5—H50.9300
N1—C51.359 (4)C6—H6A0.9600
N1—C21.387 (4)C6—H6B0.9600
N1—C61.472 (4)C6—H6C0.9600
N2—O31.227 (4)C7—C81.465 (4)
N2—O21.232 (4)C7—H70.9300
N2—C41.439 (4)C8—C91.387 (4)
N3—C11.354 (4)C8—C131.402 (4)
N3—N41.386 (3)C9—C101.383 (5)
N3—H30.8600C10—C111.379 (5)
N4—C71.276 (4)C10—H100.9300
O1—C11.234 (3)C11—C121.374 (5)
C1—C21.483 (4)C11—H110.9300
C2—C31.374 (4)C12—C131.388 (4)
C3—C41.397 (4)C12—H120.9300
C3—H3A0.9300C13—H130.9300
C4—C51.369 (5)
C5—N1—C2108.5 (3)N1—C6—H6B109.5
C5—N1—C6124.2 (3)H6A—C6—H6B109.5
C2—N1—C6127.1 (2)N1—C6—H6C109.5
O3—N2—O2124.7 (3)H6A—C6—H6C109.5
O3—N2—C4118.2 (4)H6B—C6—H6C109.5
O2—N2—C4117.1 (3)N4—C7—C8120.8 (3)
C1—N3—N4119.4 (2)N4—C7—H7119.6
C1—N3—H3120.3C8—C7—H7119.6
N4—N3—H3120.3C9—C8—C13116.7 (3)
C7—N4—N3114.6 (2)C9—C8—C7122.4 (3)
O1—C1—N3123.5 (3)C13—C8—C7120.9 (3)
O1—C1—C2123.1 (3)C10—C9—C8122.4 (3)
N3—C1—C2113.3 (3)C10—C9—Cl1118.5 (3)
C3—C2—N1108.5 (3)C8—C9—Cl1119.1 (2)
C3—C2—C1128.8 (3)C11—C10—C9119.6 (3)
N1—C2—C1122.6 (3)C11—C10—H10120.2
C2—C3—C4106.1 (3)C9—C10—H10120.2
C2—C3—H3A126.9C12—C11—C10119.8 (3)
C4—C3—H3A126.9C12—C11—H11120.1
C5—C4—C3109.2 (3)C10—C11—H11120.1
C5—C4—N2124.3 (3)C11—C12—C13120.2 (3)
C3—C4—N2126.4 (3)C11—C12—H12119.9
N1—C5—C4107.6 (3)C13—C12—H12119.9
N1—C5—H5126.2C12—C13—C8121.3 (3)
C4—C5—H5126.2C12—C13—H13119.4
N1—C6—H6A109.5C8—C13—H13119.4
C1—N3—N4—C7171.3 (3)C2—N1—C5—C41.7 (4)
N4—N3—C1—O1−0.5 (5)C6—N1—C5—C4177.5 (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—N1178.0 (3)
C6—N1—C2—C3−177.2 (3)N3—N4—C7—C8175.1 (3)
C5—N1—C2—C1−177.7 (3)N4—C7—C8—C9168.3 (3)
C6—N1—C2—C16.7 (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—C329.3 (5)C7—C8—C9—C10176.4 (4)
O1—C1—C2—N127.9 (5)C13—C8—C9—Cl1178.0 (3)
N3—C1—C2—N1−155.5 (3)C7—C8—C9—Cl1−4.9 (5)
N1—C2—C3—C40.8 (4)C8—C9—C10—C11−0.7 (6)
C1—C2—C3—C4176.6 (3)Cl1—C9—C10—C11−179.4 (3)
C2—C3—C4—C50.3 (4)C9—C10—C11—C121.2 (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—C5175.1 (4)C9—C8—C13—C121.5 (5)
O3—N2—C4—C3172.3 (3)C7—C8—C13—C12−175.6 (3)
O2—N2—C4—C3−5.9 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O1i0.862.142.941 (3)154
Symmetry code: (i) x, −y+3/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O1i0.8602.1442.941 (3)154.03
Symmetry code: (i) x, −y+3/2, z+1/2.
 

Acknowledgements

This work was supported by the National-level College Students' Innovative Training Plan Program of the People's Republic of China (grant No. 201310122001) and the Scientific Research Foundation for PhDs of Changzhi University.

References

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ISSN: 2056-9890
Volume 70| Part 1| January 2014| Page o99
https://doi.org/10.1107/S1600536813034119
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