2-Benzoyl-pyridine semicarbazone.

The title compound, C(13)H(12)N(4)O, crystallizes with two independent mol-ecules in the asymmetric unit. The compound crystallizes as the ZE isomer, where Z and E refer to the configuration around the C=N and N-C bonds, respectively, with an N-H⋯N(py) (py is pyridine) intra-molecular hydrogen bond. The dihedral angles between the least-squares planes through the semicarbazone group and the pyridyl ring are 22.70 (9) and 27.26 (9)° for the two mol-ecules. There are intermolecular N-H⋯O hydrogen bonds.

Related literature

For related literature, see: Beraldo & Gambino (2004 ▶); Beraldo et al. (2002 ▶); Teixeira et al. (2003 ▶); Farrell (2002 ▶); Pérez-Rebolledo et al. (2006 ▶).

Experimental

Crystal data

C13H12N4O

M = 240.27

Monoclinic,

a = 22.9281 (7) Å

b = 9.1868 (2) Å

c = 23.1869 (7) Å

β = 93.049 (1)°

V = 4877.1 (2) Å3

Z = 16

Mo Kα radiation

μ = 0.09 mm−1

T = 294 K

0.18 × 0.14 × 0.04 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

16551 measured reflections

4588 independent reflections

3011 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.150

S = 1.07

4588 reflections

325 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.22 e Å−3

Data collection: COLLECT (Enraf–Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DEn class="Chemical">NZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807064628/ww2110sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064628/ww2110Isup2.hkl

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

C13H12N4O	F000 = 2016
Mr = 240.27	Dx = 1.309 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 23344 reflections
a = 22.9281 (7) Å	θ = 2.9–25.7º
b = 9.1868 (2) Å	µ = 0.09 mm−1
c = 23.1869 (7) Å	T = 294 K
β = 93.049 (1)º	Prism, colourless
V = 4877.1 (2) Å3	0.18 × 0.14 × 0.04 mm
Z = 16

KappaCCD diffractometer	Rint = 0.066
T = 294 K	θmax = 25.7º
φ scans and ω scans with κ offsets	θmin = 3.5º
Absorption correction: none	h = −27→27
16551 measured reflections	k = −10→11
4588 independent reflections	l = −28→28
3011 reflections with I > 2σ(I)

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0842P)2] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.047	(Δ/σ)max < 0.001
wR(F2) = 0.150	Δρmax = 0.27 e Å−3
S = 1.07	Δρmin = −0.22 e Å−3
4588 reflections	Extinction correction: none
325 parameters

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.

	x	y	z	Uiso*/Ueq
O1	0.32552 (5)	0.15282 (12)	0.00628 (6)	0.0579 (4)
N11	0.30310 (7)	0.38523 (15)	0.02708 (7)	0.0638 (5)
H11A	0.2668	0.3735	0.0168	0.077*
H11B	0.3154	0.4685	0.0396	0.077*
N12	0.39721 (7)	0.30226 (14)	0.03898 (7)	0.0560 (4)
H12	0.4234	0.2373	0.0338	0.067*
N13	0.41230 (6)	0.43452 (15)	0.06270 (6)	0.0518 (4)
N14	0.50663 (7)	0.22107 (17)	0.07080 (8)	0.0646 (5)
C11	0.33995 (8)	0.27542 (18)	0.02374 (8)	0.0472 (4)
C12	0.46602 (8)	0.46234 (18)	0.07889 (7)	0.0503 (4)
C13	0.47417 (8)	0.60980 (18)	0.10515 (8)	0.0507 (5)
C14	0.43912 (9)	0.7256 (2)	0.08574 (9)	0.0615 (5)
H14	0.4120	0.7117	0.0550	0.074*
C15	0.44422 (10)	0.8602 (2)	0.11153 (11)	0.0717 (6)
H15	0.4210	0.9369	0.0977	0.086*
C16	0.48359 (10)	0.8818 (2)	0.15773 (11)	0.0752 (6)
H16	0.4864	0.9723	0.1756	0.090*
C17	0.51862 (10)	0.7691 (2)	0.17715 (10)	0.0728 (6)
H17	0.5458	0.7840	0.2078	0.087*
C18	0.51390 (9)	0.6347 (2)	0.15160 (9)	0.0612 (5)
H18	0.5376	0.5590	0.1655	0.073*
C19	0.51699 (8)	0.36475 (18)	0.07344 (8)	0.0526 (5)
C110	0.57304 (9)	0.4197 (2)	0.07022 (8)	0.0625 (5)
H110	0.5795	0.5196	0.0709	0.075*
C111	0.61896 (9)	0.3247 (3)	0.06597 (10)	0.0745 (6)
H111	0.6568	0.3601	0.0642	0.089*
C112	0.60892 (10)	0.1782 (3)	0.06428 (10)	0.0746 (6)
H112	0.6395	0.1124	0.0620	0.090*
C113	0.55268 (10)	0.1312 (2)	0.06610 (10)	0.0732 (6)
H113	0.5456	0.0316	0.0640	0.088*
O2	0.24288 (6)	0.15322 (12)	0.42544 (5)	0.0583 (4)
N21	0.21621 (7)	0.38036 (15)	0.44999 (7)	0.0600 (4)
H21A	0.2252	0.3660	0.4860	0.072*
H21B	0.2025	0.4632	0.4386	0.072*
N22	0.20957 (7)	0.30602 (15)	0.35554 (6)	0.0568 (4)
H22	0.2161	0.2435	0.3291	0.068*
N23	0.18510 (7)	0.43784 (15)	0.34154 (6)	0.0529 (4)
N24	0.17683 (8)	0.22916 (17)	0.24561 (7)	0.0621 (4)
C21	0.22340 (8)	0.27519 (17)	0.41217 (7)	0.0468 (4)
C22	0.17017 (8)	0.46887 (18)	0.28832 (7)	0.0507 (4)
C23	0.14314 (8)	0.61504 (18)	0.28004 (8)	0.0517 (5)
C24	0.16044 (9)	0.7306 (2)	0.31577 (9)	0.0618 (5)
H24	0.1901	0.7173	0.3442	0.074*
C25	0.13392 (11)	0.8647 (2)	0.30944 (9)	0.0726 (6)
H25	0.1458	0.9412	0.3336	0.087*
C26	0.09007 (11)	0.8860 (2)	0.26773 (10)	0.0758 (7)
H26	0.0722	0.9765	0.2637	0.091*
C27	0.07268 (10)	0.7732 (2)	0.23192 (10)	0.0720 (6)
H27	0.0430	0.7876	0.2035	0.086*
C28	0.09885 (9)	0.6396 (2)	0.23788 (9)	0.0620 (5)
H28	0.0868	0.5641	0.2133	0.074*
C29	0.17786 (8)	0.37337 (19)	0.23733 (8)	0.0532 (5)
C210	0.18628 (9)	0.4333 (2)	0.18346 (8)	0.0666 (6)
H210	0.1890	0.5336	0.1790	0.080*
C211	0.19057 (11)	0.3423 (3)	0.13692 (10)	0.0781 (6)
H211	0.1953	0.3808	0.1004	0.094*
C212	0.18792 (10)	0.1954 (3)	0.14452 (10)	0.0742 (6)
H212	0.1901	0.1324	0.1133	0.089*
C213	0.18198 (10)	0.1423 (2)	0.19957 (10)	0.0717 (6)
H213	0.1815	0.0420	0.2050	0.086*

	U11	U22	U33	U12	U13	U23
O1	0.0576 (8)	0.0475 (7)	0.0680 (9)	−0.0063 (6)	−0.0032 (6)	−0.0060 (6)
N11	0.0486 (10)	0.0495 (9)	0.0915 (13)	0.0005 (7)	−0.0132 (9)	−0.0110 (8)
N12	0.0465 (10)	0.0483 (9)	0.0721 (11)	0.0010 (6)	−0.0058 (8)	−0.0077 (7)
N13	0.0498 (10)	0.0488 (8)	0.0559 (10)	−0.0047 (6)	−0.0052 (7)	0.0005 (6)
N14	0.0537 (11)	0.0583 (10)	0.0818 (13)	0.0034 (8)	0.0039 (9)	0.0122 (8)
C11	0.0461 (11)	0.0498 (10)	0.0451 (10)	−0.0030 (8)	−0.0023 (8)	−0.0002 (8)
C12	0.0466 (11)	0.0546 (11)	0.0489 (11)	−0.0046 (8)	−0.0059 (8)	0.0086 (8)
C13	0.0464 (11)	0.0526 (10)	0.0524 (11)	−0.0071 (8)	−0.0034 (8)	0.0037 (8)
C14	0.0532 (12)	0.0604 (12)	0.0695 (14)	−0.0044 (9)	−0.0093 (10)	−0.0010 (9)
C15	0.0604 (14)	0.0597 (12)	0.0945 (18)	0.0003 (9)	0.0013 (12)	−0.0048 (11)
C16	0.0682 (16)	0.0723 (14)	0.0859 (17)	−0.0156 (11)	0.0104 (12)	−0.0246 (12)
C17	0.0649 (15)	0.0865 (15)	0.0660 (14)	−0.0142 (12)	−0.0055 (11)	−0.0133 (11)
C18	0.0572 (13)	0.0693 (13)	0.0558 (12)	−0.0072 (9)	−0.0076 (10)	−0.0003 (9)
C19	0.0492 (12)	0.0595 (11)	0.0486 (11)	−0.0013 (8)	−0.0026 (8)	0.0096 (8)
C110	0.0531 (13)	0.0725 (12)	0.0616 (13)	−0.0041 (10)	0.0008 (9)	0.0043 (10)
C111	0.0470 (13)	0.0974 (17)	0.0794 (16)	0.0036 (11)	0.0073 (11)	0.0075 (12)
C112	0.0556 (14)	0.0909 (17)	0.0780 (16)	0.0163 (11)	0.0093 (11)	0.0196 (12)
C113	0.0645 (15)	0.0662 (13)	0.0893 (17)	0.0127 (10)	0.0092 (12)	0.0157 (11)
O2	0.0712 (10)	0.0462 (7)	0.0562 (8)	0.0068 (6)	−0.0069 (7)	0.0044 (6)
N21	0.0811 (12)	0.0497 (9)	0.0476 (9)	0.0128 (7)	−0.0106 (8)	0.0001 (7)
N22	0.0737 (11)	0.0499 (9)	0.0458 (9)	0.0109 (7)	−0.0049 (8)	0.0016 (6)
N23	0.0589 (10)	0.0485 (9)	0.0504 (9)	0.0032 (7)	−0.0049 (7)	0.0065 (7)
N24	0.0722 (12)	0.0599 (10)	0.0539 (10)	−0.0070 (8)	0.0013 (8)	−0.0043 (7)
C21	0.0481 (11)	0.0459 (10)	0.0456 (11)	−0.0006 (8)	−0.0034 (8)	0.0045 (8)
C22	0.0531 (11)	0.0530 (10)	0.0454 (11)	−0.0011 (8)	−0.0022 (8)	0.0062 (8)
C23	0.0523 (12)	0.0555 (11)	0.0469 (11)	0.0013 (8)	−0.0012 (9)	0.0085 (8)
C24	0.0688 (14)	0.0627 (12)	0.0528 (12)	0.0030 (10)	−0.0063 (10)	0.0011 (9)
C25	0.0964 (18)	0.0580 (13)	0.0632 (14)	0.0093 (11)	0.0034 (12)	−0.0002 (9)
C26	0.0908 (18)	0.0693 (14)	0.0678 (15)	0.0263 (12)	0.0102 (12)	0.0162 (11)
C27	0.0681 (15)	0.0846 (15)	0.0623 (14)	0.0175 (11)	−0.0046 (11)	0.0153 (11)
C28	0.0623 (13)	0.0638 (12)	0.0587 (13)	0.0021 (9)	−0.0074 (10)	0.0078 (9)
C29	0.0502 (12)	0.0589 (12)	0.0500 (11)	−0.0016 (8)	−0.0030 (8)	0.0028 (8)
C210	0.0732 (15)	0.0745 (13)	0.0524 (13)	0.0056 (10)	0.0058 (10)	0.0077 (10)
C211	0.0852 (18)	0.0993 (18)	0.0504 (13)	0.0141 (13)	0.0088 (11)	0.0019 (11)
C212	0.0694 (15)	0.0977 (18)	0.0557 (14)	0.0032 (12)	0.0037 (11)	−0.0171 (11)
C213	0.0772 (16)	0.0686 (13)	0.0690 (15)	−0.0080 (10)	0.0019 (12)	−0.0112 (11)

O1—C11	1.2360 (19)	O2—C21	1.2390 (19)
N11—C11	1.321 (2)	N21—C21	1.321 (2)
N11—H11A	0.8600	N21—H21A	0.8600
N11—H11B	0.8600	N21—H21B	0.8600
N12—C11	1.364 (2)	N22—C21	1.364 (2)
N12—N13	1.3705 (19)	N22—N23	1.3665 (18)
N12—H12	0.8600	N22—H22	0.8600
N13—C12	1.294 (2)	N23—C22	1.295 (2)
N14—C19	1.342 (2)	N24—C29	1.339 (2)
N14—C113	1.349 (3)	N24—C213	1.343 (3)
C12—C19	1.484 (2)	C22—C23	1.487 (2)
C12—C13	1.493 (2)	C22—C29	1.490 (2)
C13—C18	1.392 (2)	C23—C28	1.390 (2)
C13—C14	1.393 (3)	C23—C24	1.392 (3)
C14—C15	1.376 (3)	C24—C25	1.378 (3)
C14—H14	0.9300	C24—H24	0.9300
C15—C16	1.378 (3)	C25—C26	1.371 (3)
C15—H15	0.9300	C25—H25	0.9300
C16—C17	1.371 (3)	C26—C27	1.374 (3)
C16—H16	0.9300	C26—H26	0.9300
C17—C18	1.371 (3)	C27—C28	1.370 (3)
C17—H17	0.9300	C27—H27	0.9300
C18—H18	0.9300	C28—H28	0.9300
C19—C110	1.386 (3)	C29—C210	1.388 (3)
C110—C111	1.375 (3)	C210—C211	1.372 (3)
C110—H110	0.9300	C210—H210	0.9300
C111—C112	1.366 (3)	C211—C212	1.363 (3)
C111—H111	0.9300	C211—H211	0.9300
C112—C113	1.362 (3)	C212—C213	1.380 (3)
C112—H112	0.9300	C212—H212	0.9300
C113—H113	0.9300	C213—H213	0.9300
C11—N11—H11A	120.0	C21—N21—H21A	120.0
C11—N11—H11B	120.0	C21—N21—H21B	120.0
H11A—N11—H11B	120.0	H21A—N21—H21B	120.0
C11—N12—N13	118.90 (14)	C21—N22—N23	118.96 (14)
C11—N12—H12	120.6	C21—N22—H22	120.5
N13—N12—H12	120.6	N23—N22—H22	120.5
C12—N13—N12	120.51 (15)	C22—N23—N22	120.40 (14)
C19—N14—C113	117.91 (17)	C29—N24—C213	118.09 (17)
O1—C11—N11	123.66 (17)	O2—C21—N21	123.56 (16)
O1—C11—N12	119.14 (15)	O2—C21—N22	119.28 (15)
N11—C11—N12	117.18 (15)	N21—C21—N22	117.14 (14)
N13—C12—C19	126.72 (16)	N23—C22—C23	114.15 (15)
N13—C12—C13	113.21 (15)	N23—C22—C29	126.16 (15)
C19—C12—C13	120.07 (15)	C23—C22—C29	119.68 (15)
C18—C13—C14	117.82 (16)	C28—C23—C24	117.99 (16)
C18—C13—C12	121.83 (16)	C28—C23—C22	121.42 (16)
C14—C13—C12	120.23 (16)	C24—C23—C22	120.56 (16)
C15—C14—C13	120.76 (19)	C25—C24—C23	120.56 (19)
C15—C14—H14	119.6	C25—C24—H24	119.7
C13—C14—H14	119.6	C23—C24—H24	119.7
C14—C15—C16	120.3 (2)	C26—C25—C24	120.4 (2)
C14—C15—H15	119.8	C26—C25—H25	119.8
C16—C15—H15	119.8	C24—C25—H25	119.8
C17—C16—C15	119.63 (19)	C25—C26—C27	119.81 (19)
C17—C16—H16	120.2	C25—C26—H26	120.1
C15—C16—H16	120.2	C27—C26—H26	120.1
C16—C17—C18	120.4 (2)	C28—C27—C26	120.2 (2)
C16—C17—H17	119.8	C28—C27—H27	119.9
C18—C17—H17	119.8	C26—C27—H27	119.9
C17—C18—C13	121.05 (19)	C27—C28—C23	121.07 (19)
C17—C18—H18	119.5	C27—C28—H28	119.5
C13—C18—H18	119.5	C23—C28—H28	119.5
N14—C19—C110	121.19 (17)	N24—C29—C210	121.71 (17)
N14—C19—C12	117.39 (16)	N24—C29—C22	117.71 (16)
C110—C19—C12	121.42 (16)	C210—C29—C22	120.57 (17)
C111—C110—C19	119.2 (2)	C211—C210—C29	119.1 (2)
C111—C110—H110	120.4	C211—C210—H210	120.5
C19—C110—H110	120.4	C29—C210—H210	120.5
C112—C111—C110	119.9 (2)	C212—C211—C210	119.7 (2)
C112—C111—H111	120.0	C212—C211—H211	120.1
C110—C111—H111	120.0	C210—C211—H211	120.1
C113—C112—C111	118.0 (2)	C211—C212—C213	118.48 (19)
C113—C112—H112	121.0	C211—C212—H212	120.8
C111—C112—H112	121.0	C213—C212—H212	120.8
N14—C113—C112	123.7 (2)	N24—C213—C212	122.8 (2)
N14—C113—H113	118.1	N24—C213—H213	118.6
C112—C113—H113	118.1	C212—C213—H213	118.6
C11—N12—N13—C12	178.38 (16)	C21—N22—N23—C22	−178.29 (16)
N13—N12—C11—O1	−174.77 (15)	N23—N22—C21—O2	176.43 (15)
N13—N12—C11—N11	7.2 (2)	N23—N22—C21—N21	−5.0 (2)
N12—N13—C12—C19	1.8 (3)	N22—N23—C22—C23	178.90 (15)
N12—N13—C12—C13	−178.45 (15)	N22—N23—C22—C29	−1.2 (3)
N13—C12—C13—C18	142.89 (18)	N23—C22—C23—C28	−145.14 (19)
C19—C12—C13—C18	−37.3 (3)	C29—C22—C23—C28	34.9 (3)
N13—C12—C13—C14	−33.1 (2)	N23—C22—C23—C24	32.8 (3)
C19—C12—C13—C14	146.70 (18)	C29—C22—C23—C24	−147.07 (18)
C18—C13—C14—C15	0.6 (3)	C28—C23—C24—C25	0.4 (3)
C12—C13—C14—C15	176.71 (19)	C22—C23—C24—C25	−177.65 (18)
C13—C14—C15—C16	−1.1 (3)	C23—C24—C25—C26	0.0 (3)
C14—C15—C16—C17	1.4 (3)	C24—C25—C26—C27	−0.3 (3)
C15—C16—C17—C18	−1.2 (3)	C25—C26—C27—C28	0.2 (3)
C16—C17—C18—C13	0.8 (3)	C26—C27—C28—C23	0.2 (3)
C14—C13—C18—C17	−0.4 (3)	C24—C23—C28—C27	−0.5 (3)
C12—C13—C18—C17	−176.51 (18)	C22—C23—C28—C27	177.56 (19)
C113—N14—C19—C110	1.3 (3)	C213—N24—C29—C210	−2.5 (3)
C113—N14—C19—C12	−179.70 (17)	C213—N24—C29—C22	178.06 (18)
N13—C12—C19—N14	−24.8 (3)	N23—C22—C29—N24	29.3 (3)
C13—C12—C19—N14	155.40 (16)	C23—C22—C29—N24	−150.77 (17)
N13—C12—C19—C110	154.13 (19)	N23—C22—C29—C210	−150.11 (19)
C13—C12—C19—C110	−25.6 (3)	C23—C22—C29—C210	29.8 (3)
N14—C19—C110—C111	−1.9 (3)	N24—C29—C210—C211	3.5 (3)
C12—C19—C110—C111	179.14 (18)	C22—C29—C210—C211	−177.08 (19)
C19—C110—C111—C112	0.8 (3)	C29—C210—C211—C212	−1.6 (3)
C110—C111—C112—C113	0.9 (3)	C210—C211—C212—C213	−1.2 (3)
C19—N14—C113—C112	0.4 (3)	C29—N24—C213—C212	−0.4 (3)
C111—C112—C113—N14	−1.6 (3)	C211—C212—C213—N24	2.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11A···O1i	0.86	2.17	3.029 (2)	178
N11—H11B···O2ii	0.86	2.33	2.917 (2)	126
N21—H21B···O1ii	0.86	2.27	2.883 (2)	128
N21—H21A···O2iii	0.86	2.15	3.005 (2)	173
N12—H12···N14	0.86	2.06	2.683 (2)	129
N22—H22···N24	0.86	2.10	2.712 (2)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H11A⋯O1i	0.86	2.17	3.029 (2)	178
N11—H11B⋯O2ii	0.86	2.33	2.917 (2)	126
N21—H21B⋯O1ii	0.86	2.27	2.883 (2)	128
N21—H21A⋯O2iii	0.86	2.15	3.005 (2)	173
N12—H12⋯N14	0.86	2.06	2.683 (2)	129
N22—H22⋯N24	0.86	2.10	2.712 (2)	128

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