N'-[(E)-(1-Methyl-1H-pyrrol-2-yl)methyl-idene]pyridine-4-carbohydrazide.

In the title compound, C(12)H(12)N(4)O, the pyridine and pyrrole rings are inclined at an angle of 29.22 (8)° and an intra-molecular C-H⋯N inter-action geneates an S(6) ring. In the crystal, mol-ecules are linked by N-H⋯N hydrogen bonds, forming (010) C(7) chains. The chains are cross-linked by weak C-H⋯O inter-actions, which generate R(2) (2)(18) ring motifs within an infinite sheet. Finally, two C-H⋯π inter-actions are present, where the C-H groups are from the pyridine ring and π is the pyrrole ring.

Related literature

For background information on Schiff bases containing heterocyclic rings and for related structures, see: Shafiq et al.,(2009a ▶,b ▶); Hussain et al. (2010 ▶) For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C12H12N4O

M = 228.26

Monoclinic,

a = 8.2134 (3) Å

b = 10.6740 (4) Å

c = 13.1332 (4) Å

β = 96.938 (2)°

V = 1142.95 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.24 × 0.18 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.980, T max = 0.985

12030 measured reflections

2803 independent reflections

2023 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.127

S = 1.04

2803 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810025341/hb5530sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025341/hb5530Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H12N4O	F(000) = 480
Mr = 228.26	Dx = 1.326 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1770 reflections
a = 8.2134 (3) Å	θ = 2.6–28.4°
b = 10.6740 (4) Å	µ = 0.09 mm−1
c = 13.1332 (4) Å	T = 296 K
β = 96.938 (2)°	Prism, red
V = 1142.95 (7) Å3	0.24 × 0.18 × 0.15 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2803 independent reflections
Radiation source: fine-focus sealed tube	2023 reflections with I > 2σ(I)
graphite	Rint = 0.029
Detector resolution: 7.50 pixels mm-1	θmax = 28.3°, θmin = 2.5°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −14→14
Tmin = 0.980, Tmax = 0.985	l = −17→17
12030 measured reflections

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0618P)2 + 0.235P] where P = (Fo2 + 2Fc2)/3
2803 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O1	0.68517 (16)	0.25900 (11)	0.46989 (10)	0.0596 (4)
N1	0.25031 (16)	0.01556 (12)	0.25463 (10)	0.0424 (4)
N2	0.55170 (15)	0.41010 (11)	0.37015 (10)	0.0388 (4)
N3	0.65784 (16)	0.50489 (12)	0.40795 (10)	0.0417 (4)
N4	0.85194 (16)	0.74061 (12)	0.46127 (10)	0.0411 (4)
C1	0.46019 (16)	0.19827 (12)	0.34909 (10)	0.0315 (4)
C2	0.40449 (19)	0.10059 (13)	0.40461 (11)	0.0374 (4)
C3	0.30152 (19)	0.01259 (14)	0.35500 (12)	0.0414 (5)
C4	0.3056 (2)	0.11012 (14)	0.20128 (11)	0.0421 (5)
C5	0.40918 (19)	0.20229 (14)	0.24441 (11)	0.0378 (4)
C6	0.57736 (18)	0.29160 (14)	0.40312 (11)	0.0371 (4)
C7	0.62947 (19)	0.61063 (14)	0.36395 (12)	0.0416 (5)
C8	0.72195 (19)	0.72388 (14)	0.38651 (12)	0.0404 (5)
C9	0.6991 (2)	0.83500 (15)	0.33312 (13)	0.0497 (5)
C10	0.8163 (2)	0.92006 (16)	0.37628 (13)	0.0539 (6)
C11	0.9081 (2)	0.85957 (15)	0.45424 (13)	0.0496 (6)
C12	0.9127 (2)	0.65484 (17)	0.54194 (14)	0.0574 (6)
H2	0.46924	0.42717	0.32551	0.0466*
H2A	0.43635	0.09445	0.47482	0.0449*
H3	0.26551	−0.05268	0.39352	0.0497*
H4	0.27213	0.11375	0.13112	0.0505*
H5	0.44438	0.26614	0.20412	0.0454*
H7	0.54104	0.61488	0.31268	0.0500*
H9	0.61937	0.85044	0.27801	0.0597*
H10	0.82924	1.00246	0.35569	0.0646*
H11	0.99575	0.89429	0.49628	0.0595*
H12A	0.86108	0.67234	0.60217	0.0860*
H12B	1.02928	0.66469	0.55737	0.0860*
H12C	0.88828	0.57043	0.51995	0.0860*

	U11	U22	U33	U12	U13	U23
O1	0.0566 (8)	0.0471 (7)	0.0666 (8)	−0.0071 (6)	−0.0275 (6)	0.0054 (6)
N1	0.0438 (8)	0.0334 (7)	0.0475 (7)	−0.0070 (6)	−0.0048 (5)	−0.0019 (5)
N2	0.0359 (7)	0.0296 (6)	0.0480 (7)	−0.0057 (5)	−0.0070 (5)	−0.0040 (5)
N3	0.0389 (7)	0.0336 (7)	0.0511 (7)	−0.0081 (5)	−0.0010 (5)	−0.0087 (5)
N4	0.0427 (7)	0.0335 (7)	0.0474 (7)	−0.0083 (5)	0.0062 (6)	−0.0074 (5)
C1	0.0297 (7)	0.0266 (7)	0.0374 (7)	0.0006 (5)	0.0003 (5)	−0.0018 (5)
C2	0.0437 (8)	0.0331 (8)	0.0340 (7)	−0.0001 (6)	−0.0012 (6)	0.0025 (6)
C3	0.0458 (9)	0.0331 (8)	0.0449 (8)	−0.0071 (7)	0.0035 (6)	0.0052 (6)
C4	0.0509 (9)	0.0385 (8)	0.0341 (7)	−0.0045 (7)	−0.0061 (6)	−0.0011 (6)
C5	0.0453 (9)	0.0318 (7)	0.0359 (7)	−0.0047 (6)	0.0030 (6)	0.0032 (6)
C6	0.0348 (8)	0.0343 (8)	0.0406 (7)	−0.0037 (6)	−0.0022 (6)	−0.0022 (6)
C7	0.0380 (8)	0.0344 (8)	0.0509 (9)	−0.0047 (7)	−0.0012 (7)	−0.0074 (7)
C8	0.0396 (8)	0.0351 (8)	0.0470 (8)	−0.0051 (6)	0.0069 (7)	−0.0087 (6)
C9	0.0580 (10)	0.0381 (9)	0.0529 (9)	−0.0047 (8)	0.0064 (8)	−0.0029 (7)
C10	0.0729 (12)	0.0331 (8)	0.0580 (10)	−0.0118 (8)	0.0178 (9)	−0.0040 (7)
C11	0.0560 (10)	0.0380 (9)	0.0570 (10)	−0.0198 (8)	0.0162 (8)	−0.0155 (8)
C12	0.0538 (11)	0.0461 (10)	0.0680 (11)	−0.0058 (8)	−0.0098 (8)	0.0025 (9)

O1—C6	1.219 (2)	C7—C8	1.439 (2)
N1—C3	1.335 (2)	C8—C9	1.379 (2)
N1—C4	1.339 (2)	C9—C10	1.393 (2)
N2—N3	1.3877 (18)	C10—C11	1.359 (2)
N2—C6	1.3453 (19)	C2—H2A	0.9300
N3—C7	1.277 (2)	C3—H3	0.9300
N4—C8	1.372 (2)	C4—H4	0.9300
N4—C11	1.358 (2)	C5—H5	0.9300
N4—C12	1.443 (2)	C7—H7	0.9300
N2—H2	0.8600	C9—H9	0.9300
C1—C2	1.3815 (19)	C10—H10	0.9300
C1—C5	1.3886 (19)	C11—H11	0.9300
C1—C6	1.502 (2)	C12—H12A	0.9600
C2—C3	1.374 (2)	C12—H12B	0.9600
C4—C5	1.377 (2)	C12—H12C	0.9600
C3—N1—C4	116.64 (13)	N4—C11—C10	109.47 (15)
N3—N2—C6	120.21 (12)	C1—C2—H2A	120.00
N2—N3—C7	114.22 (13)	C3—C2—H2A	120.00
C8—N4—C11	108.33 (13)	N1—C3—H3	118.00
C8—N4—C12	127.81 (13)	C2—C3—H3	118.00
C11—N4—C12	123.58 (14)	N1—C4—H4	118.00
C6—N2—H2	120.00	C5—C4—H4	118.00
N3—N2—H2	120.00	C1—C5—H5	121.00
C2—C1—C6	119.03 (12)	C4—C5—H5	121.00
C2—C1—C5	117.80 (13)	N3—C7—H7	117.00
C5—C1—C6	123.13 (12)	C8—C7—H7	117.00
C1—C2—C3	119.32 (13)	C8—C9—H9	126.00
N1—C3—C2	123.67 (14)	C10—C9—H9	126.00
N1—C4—C5	123.72 (14)	C9—C10—H10	127.00
C1—C5—C4	118.86 (13)	C11—C10—H10	127.00
N2—C6—C1	113.89 (12)	N4—C11—H11	125.00
O1—C6—N2	124.87 (14)	C10—C11—H11	125.00
O1—C6—C1	121.24 (13)	N4—C12—H12A	109.00
N3—C7—C8	125.91 (15)	N4—C12—H12B	109.00
N4—C8—C9	107.35 (13)	N4—C12—H12C	109.00
C7—C8—C9	125.57 (15)	H12A—C12—H12B	109.00
N4—C8—C7	127.04 (14)	H12A—C12—H12C	109.00
C8—C9—C10	107.99 (15)	H12B—C12—H12C	109.00
C9—C10—C11	106.87 (15)
C4—N1—C3—C2	0.6 (2)	C2—C1—C5—C4	0.4 (2)
C3—N1—C4—C5	−0.5 (2)	C6—C1—C5—C4	177.90 (14)
C6—N2—N3—C7	173.81 (14)	C2—C1—C6—O1	38.1 (2)
N3—N2—C6—O1	4.1 (2)	C2—C1—C6—N2	−142.47 (14)
N3—N2—C6—C1	−175.38 (12)	C5—C1—C6—O1	−139.38 (16)
N2—N3—C7—C8	−178.82 (14)	C5—C1—C6—N2	40.08 (19)
C11—N4—C8—C7	177.64 (15)	C1—C2—C3—N1	−0.2 (2)
C11—N4—C8—C9	0.04 (17)	N1—C4—C5—C1	0.0 (2)
C12—N4—C8—C7	−8.4 (3)	N3—C7—C8—N4	−2.9 (3)
C12—N4—C8—C9	174.00 (15)	N3—C7—C8—C9	174.33 (16)
C8—N4—C11—C10	0.12 (19)	N4—C8—C9—C10	−0.18 (18)
C12—N4—C11—C10	−174.15 (15)	C7—C8—C9—C10	−177.82 (15)
C5—C1—C2—C3	−0.3 (2)	C8—C9—C10—C11	0.25 (19)
C6—C1—C2—C3	−177.89 (14)	C9—C10—C11—N4	−0.23 (19)

Cg1 is the centroid of the C8—C11/N4 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1i	0.86	2.19	3.0205 (18)	163
C4—H4···O1ii	0.93	2.54	3.3821 (19)	150
C12—H12B···O1iii	0.96	2.55	3.450 (2)	156
C12—H12C···N3	0.96	2.36	3.025 (2)	126
C2—H2A···Cg1iv	0.93	2.83	3.3258 (16)	114
C5—H5···Cg1v	0.93	2.71	3.4669 (17)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8—C11/N4 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N1i	0.86	2.19	3.0205 (18)	163
C4—H4⋯O1ii	0.93	2.54	3.3821 (19)	150
C12—H12B⋯O1iii	0.96	2.55	3.450 (2)	156
C12—H12C⋯N3	0.96	2.36	3.025 (2)	126
C2—H2A⋯Cg1iv	0.93	2.83	3.3258 (16)	114
C5—H5⋯Cg1v	0.93	2.71	3.4669 (17)	139

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .