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

In the title compound, C(13)H(13)N(3)O, the phenyl and pyrrole rings are inclined at 47.45 (8)°. In the crystal, inter-molecular N-H⋯O and C-H⋯O hydrogen bonds form R(2) (1)(6) ring motifs. Mol-ecules connected through these hydrogen bonds are arranged into polymeric chains extending along the c axis.

Related literature

For related structures, see: Shafiq et al. (2009a ▶,b ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H13N3O

M = 227.26

Monoclinic,

a = 11.1170 (8) Å

b = 11.6329 (9) Å

c = 9.6735 (6) Å

β = 110.241 (3)°

V = 1173.75 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.28 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.942, T max = 0.952

11164 measured reflections

2930 independent reflections

1770 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.139

S = 1.02

2930 reflections

155 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 (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/S1600536810025390/gk2289sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025390/gk2289Isup2.hkl

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

C13H13N3O	F(000) = 480
Mr = 227.26	Dx = 1.286 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1770 reflections
a = 11.1170 (8) Å	θ = 2.6–28.4°
b = 11.6329 (9) Å	µ = 0.09 mm−1
c = 9.6735 (6) Å	T = 296 K
β = 110.241 (3)°	Needle, colorless
V = 1173.75 (15) Å3	0.28 × 0.12 × 0.10 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2930 independent reflections
Radiation source: fine-focus sealed tube	1770 reflections with I > 2σ(I)
graphite	Rint = 0.047
Detector resolution: 7.50 pixels mm-1	θmax = 28.4°, θmin = 2.6°
ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −15→15
Tmin = 0.942, Tmax = 0.952	l = −12→9
11164 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0555P)2 + 0.160P] where P = (Fo2 + 2Fc2)/3
2930 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.16 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	0.71496 (14)	0.18682 (11)	0.12223 (13)	0.0554 (5)
N1	0.75685 (15)	0.26311 (12)	0.34764 (15)	0.0431 (5)
N2	0.80816 (15)	0.36186 (12)	0.30879 (16)	0.0442 (5)
N3	0.93230 (15)	0.58927 (13)	0.29335 (16)	0.0457 (5)
C1	0.66632 (16)	0.07206 (14)	0.29906 (18)	0.0394 (5)
C2	0.67749 (19)	0.05014 (16)	0.4433 (2)	0.0492 (7)
C3	0.6323 (2)	−0.05186 (18)	0.4795 (2)	0.0602 (8)
C4	0.5752 (2)	−0.13174 (18)	0.3738 (3)	0.0639 (8)
C5	0.5635 (2)	−0.11093 (19)	0.2302 (3)	0.0695 (9)
C6	0.6095 (2)	−0.01047 (18)	0.1927 (2)	0.0565 (7)
C7	0.71456 (16)	0.17851 (14)	0.24946 (19)	0.0389 (6)
C8	0.80671 (18)	0.44929 (15)	0.38773 (19)	0.0454 (6)
C9	0.85533 (18)	0.56059 (15)	0.37314 (19)	0.0445 (6)
C10	0.8295 (2)	0.66046 (17)	0.4330 (2)	0.0592 (8)
C11	0.8898 (2)	0.75049 (18)	0.3880 (3)	0.0657 (9)
C12	0.9521 (2)	0.70430 (16)	0.3038 (2)	0.0563 (7)
C13	0.9916 (2)	0.51144 (17)	0.2185 (2)	0.0562 (8)
H1	0.75240	0.25659	0.43429	0.0517*
H2	0.71552	0.10422	0.51611	0.0591*
H3	0.64097	−0.06633	0.57704	0.0723*
H4	0.54425	−0.19993	0.39907	0.0767*
H5	0.52429	−0.16507	0.15793	0.0833*
H6	0.60254	0.00238	0.09532	0.0679*
H8	0.77103	0.43980	0.46091	0.0545*
H10	0.78019	0.66688	0.49312	0.0711*
H11	0.88753	0.82779	0.41155	0.0788*
H12	1.00108	0.74519	0.25975	0.0676*
H13A	1.05186	0.55310	0.18654	0.0843*
H13B	0.92678	0.47841	0.13455	0.0843*
H13C	1.03550	0.45137	0.28485	0.0843*

	U11	U22	U33	U12	U13	U23
O1	0.0848 (10)	0.0528 (8)	0.0376 (7)	−0.0061 (7)	0.0325 (7)	−0.0043 (6)
N1	0.0592 (10)	0.0417 (8)	0.0346 (8)	−0.0077 (7)	0.0241 (7)	−0.0013 (6)
N2	0.0558 (10)	0.0409 (8)	0.0399 (8)	−0.0051 (7)	0.0216 (7)	0.0028 (7)
N3	0.0516 (9)	0.0408 (8)	0.0479 (9)	−0.0001 (7)	0.0214 (8)	0.0031 (7)
C1	0.0378 (9)	0.0440 (10)	0.0371 (9)	0.0005 (8)	0.0138 (8)	−0.0010 (8)
C2	0.0590 (12)	0.0476 (11)	0.0426 (11)	−0.0056 (9)	0.0195 (9)	−0.0009 (8)
C3	0.0711 (14)	0.0606 (13)	0.0520 (12)	−0.0075 (11)	0.0251 (11)	0.0097 (10)
C4	0.0647 (14)	0.0540 (13)	0.0751 (16)	−0.0136 (10)	0.0269 (12)	0.0061 (11)
C5	0.0750 (16)	0.0641 (14)	0.0675 (15)	−0.0270 (12)	0.0224 (12)	−0.0157 (12)
C6	0.0604 (13)	0.0633 (13)	0.0446 (11)	−0.0146 (10)	0.0165 (10)	−0.0064 (10)
C7	0.0418 (10)	0.0430 (10)	0.0351 (9)	0.0039 (8)	0.0175 (8)	−0.0013 (8)
C8	0.0568 (12)	0.0453 (11)	0.0388 (10)	−0.0008 (8)	0.0224 (9)	0.0022 (8)
C9	0.0548 (11)	0.0421 (10)	0.0384 (10)	0.0003 (8)	0.0185 (9)	0.0027 (8)
C10	0.0787 (15)	0.0468 (11)	0.0624 (13)	0.0016 (10)	0.0375 (12)	−0.0031 (10)
C11	0.0869 (17)	0.0394 (11)	0.0789 (16)	−0.0007 (10)	0.0391 (14)	−0.0016 (10)
C12	0.0662 (13)	0.0407 (11)	0.0668 (14)	−0.0041 (9)	0.0291 (11)	0.0076 (9)
C13	0.0645 (14)	0.0516 (12)	0.0625 (13)	−0.0037 (10)	0.0346 (11)	−0.0038 (10)

O1—C7	1.236 (2)	C9—C10	1.372 (3)
N1—N2	1.391 (2)	C10—C11	1.392 (3)
N1—C7	1.335 (2)	C11—C12	1.350 (3)
N2—C8	1.275 (2)	C2—H2	0.9300
N3—C9	1.377 (3)	C3—H3	0.9300
N3—C12	1.354 (2)	C4—H4	0.9300
N3—C13	1.452 (3)	C5—H5	0.9300
N1—H1	0.8600	C6—H6	0.9300
C1—C2	1.381 (2)	C8—H8	0.9300
C1—C7	1.493 (2)	C10—H10	0.9300
C1—C6	1.389 (3)	C11—H11	0.9300
C2—C3	1.380 (3)	C12—H12	0.9300
C3—C4	1.365 (3)	C13—H13A	0.9600
C4—C5	1.371 (4)	C13—H13B	0.9600
C5—C6	1.374 (3)	C13—H13C	0.9600
C8—C9	1.429 (3)
O1···N2	2.6801 (19)	C13···H11iii	3.0200
O1···N1i	2.910 (2)	H1···C2	2.5500
O1···C8i	3.209 (2)	H1···H2	2.0400
O1···H6	2.4500	H1···H8	2.1500
O1···H1i	2.1100	H1···O1ii	2.1100
O1···H2i	2.6400	H2···N1	2.6100
O1···H8i	2.3800	H2···H1	2.0400
N1···O1ii	2.910 (2)	H2···O1ii	2.6400
N2···N3	3.011 (2)	H2···N2ii	2.6900
N2···O1	2.6801 (19)	H2···H13Bii	2.4300
N2···C13	3.030 (3)	H3···C9ii	3.0300
N3···N2	3.011 (2)	H4···C7ix	3.0800
N1···H2	2.6100	H6···O1	2.4500
N2···H13B	2.8200	H6···C6vii	2.9600
N2···H12iii	2.7800	H6···H6vii	2.3900
N2···H2i	2.6900	H8···H1	2.1500
N2···H13C	2.8200	H8···O1ii	2.3800
C3···C3iv	3.328 (3)	H11···C13vi	3.0200
C8···O1ii	3.209 (2)	H12···H13A	2.4700
C9···C9v	3.591 (3)	H12···N2vi	2.7800
C11···C13vi	3.599 (3)	H12···H13Cvi	2.4500
C13···C11iii	3.599 (3)	H13A···H12	2.4700
C13···N2	3.030 (3)	H13A···C1vi	3.1000
C1···H13Aiii	3.1000	H13A···C7vi	2.8500
C2···H13Bii	2.7700	H13B···N2	2.8200
C2···H1	2.5500	H13B···C2i	2.7700
C6···H6vii	2.9600	H13B···H2i	2.4300
C7···H13Aiii	2.8500	H13C···N2	2.8200
C7···H4viii	3.0800	H13C···C8	3.0400
C8···H13C	3.0400	H13C···C12iii	3.0200
C9···H3i	3.0300	H13C···H12iii	2.4500
C10···H13Cv	2.9300	H13C···C10v	2.9300
C12···H13Cvi	3.0200
N2—N1—C7	119.54 (14)	C1—C2—H2	120.00
N1—N2—C8	113.93 (16)	C3—C2—H2	120.00
C9—N3—C12	108.30 (16)	C2—C3—H3	120.00
C9—N3—C13	127.28 (16)	C4—C3—H3	120.00
C12—N3—C13	124.28 (17)	C3—C4—H4	120.00
N2—N1—H1	120.00	C5—C4—H4	120.00
C7—N1—H1	120.00	C4—C5—H5	120.00
C6—C1—C7	117.20 (15)	C6—C5—H5	120.00
C2—C1—C6	118.66 (17)	C1—C6—H6	120.00
C2—C1—C7	124.13 (16)	C5—C6—H6	120.00
C1—C2—C3	120.11 (17)	N2—C8—H8	117.00
C2—C3—C4	120.73 (19)	C9—C8—H8	117.00
C3—C4—C5	119.7 (2)	C9—C10—H10	126.00
C4—C5—C6	120.3 (2)	C11—C10—H10	126.00
C1—C6—C5	120.52 (19)	C10—C11—H11	126.00
N1—C7—C1	117.39 (15)	C12—C11—H11	127.00
O1—C7—N1	121.93 (16)	N3—C12—H12	125.00
O1—C7—C1	120.68 (15)	C11—C12—H12	125.00
N2—C8—C9	125.45 (18)	N3—C13—H13A	109.00
N3—C9—C10	107.02 (16)	N3—C13—H13B	110.00
C8—C9—C10	125.74 (19)	N3—C13—H13C	110.00
N3—C9—C8	127.20 (17)	H13A—C13—H13B	109.00
C9—C10—C11	108.14 (19)	H13A—C13—H13C	109.00
C10—C11—C12	107.00 (19)	H13B—C13—H13C	109.00
N3—C12—C11	109.53 (19)
C7—N1—N2—C8	158.43 (18)	C2—C1—C7—O1	171.48 (19)
N2—N1—C7—O1	−2.8 (3)	C2—C1—C7—N1	−8.4 (3)
N2—N1—C7—C1	177.08 (16)	C6—C1—C7—O1	−7.0 (3)
N1—N2—C8—C9	178.86 (18)	C6—C1—C7—N1	173.11 (18)
C12—N3—C9—C8	177.51 (19)	C1—C2—C3—C4	−0.6 (3)
C12—N3—C9—C10	−0.4 (2)	C2—C3—C4—C5	0.5 (4)
C13—N3—C9—C8	−6.7 (3)	C3—C4—C5—C6	0.3 (4)
C13—N3—C9—C10	175.43 (18)	C4—C5—C6—C1	−1.1 (4)
C9—N3—C12—C11	−0.1 (2)	N2—C8—C9—N3	−13.0 (3)
C13—N3—C12—C11	−176.05 (19)	N2—C8—C9—C10	164.5 (2)
C6—C1—C2—C3	−0.2 (3)	N3—C9—C10—C11	0.7 (2)
C7—C1—C2—C3	−178.67 (19)	C8—C9—C10—C11	−177.2 (2)
C2—C1—C6—C5	1.1 (3)	C9—C10—C11—C12	−0.7 (3)
C7—C1—C6—C5	179.6 (2)	C10—C11—C12—N3	0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ii	0.86	2.11	2.910 (2)	155
C8—H8···O1ii	0.93	2.38	3.209 (2)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.11	2.910 (2)	155
C8—H8⋯O1i	0.93	2.38	3.209 (2)	148

Symmetry code: (i) .