Ethyl 3-methyl-4-oxo-4,5-dihydro-1H-pyrrolo[2,3-d]pyridazine-2-carboxyl-ate.

The title compound, C(10)H(11)N(3)O(3), was synthesized by the reaction of 3,5-bis-(ethoxy-carbon-yl)-2-formyl-4-methyl-1H-pyrrole and hydrazine hydrate. The angle between the pyrrole ring and the pyridazinone ring is 0.93 (9)°. In the crystal, inter-molecular N-H⋯O and N-H⋯N hydrogen-bond inter-actions link the mol-ecules into a two-dimensional network.

Related literature

For the biological activity of pyrrolopyridazine compounds, see: Chen et al. (2006 ▶); Hu et al. (2004 ▶); Swamy et al. (2005 ▶). For bond-length data, see Allen et al. (1987 ▶).

Experimental

Crystal data

C10H11N3O3

M = 221.22

Monoclinic,

a = 8.0030 (16) Å

b = 9.774 (2) Å

c = 13.370 (3) Å

β = 90.17 (3)°

V = 1045.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 295 K

0.40 × 0.26 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.959, T max = 0.994

6834 measured reflections

2045 independent reflections

1676 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.120

S = 1.06

2045 reflections

156 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker 2002 ▶); cell refinement: SAINT (Bruker 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809055081/sj2715sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055081/sj2715Isup2.hkl

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

C10H11N3O3	F(000) = 464
Mr = 221.22	Dx = 1.405 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7501 reflections
a = 8.0030 (16) Å	θ = 2.6–26.4°
b = 9.774 (2) Å	µ = 0.11 mm−1
c = 13.370 (3) Å	T = 295 K
β = 90.17 (3)°	Plate, colourless
V = 1045.8 (4) Å3	0.40 × 0.26 × 0.06 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2045 independent reflections
Radiation source: fine-focus sealed tube	1676 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.959, Tmax = 0.994	k = −11→12
6834 measured reflections	l = −16→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.120	w = 1/[σ2(Fo2) + (0.0631P)2 + 0.2196P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2045 reflections	Δρmax = 0.27 e Å−3
156 parameters	Δρmin = −0.21 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.007 (2)

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
C1	0.0960 (2)	0.38216 (17)	0.86245 (11)	0.0291 (4)
C2	0.14214 (19)	0.33040 (17)	0.95543 (11)	0.0277 (4)
C3	0.0970 (2)	0.19196 (17)	0.97885 (11)	0.0295 (4)
C4	0.0078 (2)	0.30214 (18)	0.79200 (12)	0.0348 (4)
H2	−0.0209	0.3395	0.7303	0.042*
C5	0.22621 (19)	0.43535 (17)	1.00880 (11)	0.0287 (4)
C6	0.2266 (2)	0.54646 (17)	0.94508 (11)	0.0293 (4)
C7	0.2897 (2)	0.68717 (18)	0.95437 (12)	0.0324 (4)
C8	0.4347 (2)	0.8457 (2)	1.05488 (15)	0.0473 (5)
H8A	0.3500	0.9150	1.0436	0.057*
H8B	0.5247	0.8602	1.0076	0.057*
C9	0.4995 (3)	0.8551 (3)	1.15900 (17)	0.0665 (7)
H9A	0.5831	0.7860	1.1694	0.100*
H9B	0.4094	0.8414	1.2052	0.100*
H9C	0.5478	0.9438	1.1696	0.100*
C10	0.2976 (2)	0.4242 (2)	1.11193 (12)	0.0380 (4)
H10A	0.2233	0.4670	1.1587	0.057*
H10B	0.4043	0.4690	1.1142	0.057*
H10C	0.3111	0.3295	1.1291	0.057*
N1	0.14838 (18)	0.51266 (15)	0.85690 (10)	0.0318 (4)
N2	−0.03348 (19)	0.17759 (15)	0.81245 (10)	0.0362 (4)
N3	0.01190 (19)	0.12734 (16)	0.90363 (10)	0.0349 (4)
O1	0.12783 (16)	0.13034 (12)	1.05782 (8)	0.0397 (4)
O2	0.27522 (18)	0.77051 (14)	0.88893 (10)	0.0506 (4)
O3	0.36361 (16)	0.71015 (13)	1.04147 (9)	0.0409 (4)
H1	0.132 (2)	0.565 (2)	0.8057 (15)	0.038 (5)*
H3	−0.028 (3)	0.042 (3)	0.9145 (16)	0.067 (7)*

	U11	U22	U33	U12	U13	U23
C1	0.0348 (9)	0.0251 (9)	0.0274 (8)	0.0005 (7)	−0.0006 (6)	0.0008 (7)
C2	0.0313 (8)	0.0261 (9)	0.0256 (8)	0.0013 (7)	−0.0007 (6)	0.0005 (7)
C3	0.0342 (9)	0.0275 (9)	0.0268 (8)	−0.0004 (7)	−0.0005 (6)	0.0017 (7)
C4	0.0503 (10)	0.0287 (10)	0.0253 (8)	−0.0019 (8)	−0.0054 (7)	0.0011 (7)
C5	0.0299 (8)	0.0271 (9)	0.0290 (8)	0.0013 (6)	−0.0012 (6)	−0.0003 (7)
C6	0.0321 (8)	0.0273 (9)	0.0286 (8)	−0.0002 (7)	−0.0028 (6)	−0.0013 (7)
C7	0.0347 (9)	0.0285 (10)	0.0340 (9)	−0.0017 (7)	−0.0022 (7)	−0.0007 (7)
C8	0.0492 (11)	0.0365 (12)	0.0562 (12)	−0.0114 (9)	−0.0071 (9)	−0.0098 (9)
C9	0.0655 (14)	0.0758 (18)	0.0581 (14)	−0.0170 (13)	−0.0081 (11)	−0.0236 (13)
C10	0.0447 (10)	0.0367 (11)	0.0325 (9)	−0.0025 (8)	−0.0098 (7)	0.0021 (8)
N1	0.0432 (8)	0.0254 (8)	0.0268 (7)	−0.0024 (6)	−0.0058 (6)	0.0050 (6)
N2	0.0515 (9)	0.0298 (9)	0.0272 (7)	−0.0048 (7)	−0.0059 (6)	−0.0008 (6)
N3	0.0502 (9)	0.0255 (9)	0.0290 (7)	−0.0063 (6)	−0.0053 (6)	0.0023 (6)
O1	0.0569 (8)	0.0305 (7)	0.0317 (7)	−0.0077 (6)	−0.0101 (5)	0.0078 (5)
O2	0.0723 (10)	0.0319 (8)	0.0475 (8)	−0.0113 (6)	−0.0173 (7)	0.0092 (6)
O3	0.0514 (8)	0.0324 (8)	0.0389 (7)	−0.0092 (6)	−0.0101 (6)	−0.0006 (5)

C1—N1	1.345 (2)	C7—O3	1.324 (2)
C1—C2	1.391 (2)	C8—O3	1.453 (2)
C1—C4	1.412 (2)	C8—C9	1.487 (3)
C2—C5	1.418 (2)	C8—H8A	0.9700
C2—C3	1.435 (2)	C8—H8B	0.9700
C3—O1	1.2396 (19)	C9—H9A	0.9600
C3—N3	1.368 (2)	C9—H9B	0.9600
C4—N2	1.291 (2)	C9—H9C	0.9600
C4—H2	0.9300	C10—H10A	0.9600
C5—C6	1.380 (2)	C10—H10B	0.9600
C5—C10	1.495 (2)	C10—H10C	0.9600
C6—N1	1.374 (2)	N1—H1	0.86 (2)
C6—C7	1.470 (2)	N2—N3	1.3626 (19)
C7—O2	1.201 (2)	N3—H3	0.90 (3)
N1—C1—C2	108.20 (14)	O3—C8—H8B	110.1
N1—C1—C4	130.09 (15)	C9—C8—H8B	110.1
C2—C1—C4	121.71 (16)	H8A—C8—H8B	108.4
C1—C2—C5	108.11 (15)	C8—C9—H9A	109.5
C1—C2—C3	118.14 (14)	C8—C9—H9B	109.5
C5—C2—C3	133.74 (14)	H9A—C9—H9B	109.5
O1—C3—N3	119.96 (16)	C8—C9—H9C	109.5
O1—C3—C2	126.47 (15)	H9A—C9—H9C	109.5
N3—C3—C2	113.57 (14)	H9B—C9—H9C	109.5
N2—C4—C1	120.59 (15)	C5—C10—H10A	109.5
N2—C4—H2	119.7	C5—C10—H10B	109.5
C1—C4—H2	119.7	H10A—C10—H10B	109.5
C6—C5—C2	105.10 (14)	C5—C10—H10C	109.5
C6—C5—C10	128.68 (15)	H10A—C10—H10C	109.5
C2—C5—C10	126.22 (15)	H10B—C10—H10C	109.5
N1—C6—C5	109.79 (15)	C1—N1—C6	108.79 (14)
N1—C6—C7	116.94 (14)	C1—N1—H1	123.8 (13)
C5—C6—C7	133.26 (15)	C6—N1—H1	127.4 (13)
O2—C7—O3	124.61 (16)	C4—N2—N3	117.50 (14)
O2—C7—C6	122.72 (16)	N2—N3—C3	128.49 (16)
O3—C7—C6	112.68 (14)	N2—N3—H3	112.6 (14)
O3—C8—C9	107.89 (17)	C3—N3—H3	118.8 (14)
O3—C8—H8A	110.1	C7—O3—C8	115.92 (14)
C9—C8—H8A	110.1
N1—C1—C2—C5	0.20 (18)	C10—C5—C6—C7	−1.4 (3)
C4—C1—C2—C5	−179.24 (15)	N1—C6—C7—O2	−0.1 (3)
N1—C1—C2—C3	179.22 (14)	C5—C6—C7—O2	−178.97 (18)
C4—C1—C2—C3	−0.2 (2)	N1—C6—C7—O3	−179.76 (14)
C1—C2—C3—O1	−179.84 (16)	C5—C6—C7—O3	1.3 (3)
C5—C2—C3—O1	−1.1 (3)	C2—C1—N1—C6	−0.42 (18)
C1—C2—C3—N3	0.1 (2)	C4—C1—N1—C6	178.97 (17)
C5—C2—C3—N3	178.82 (16)	C5—C6—N1—C1	0.49 (19)
N1—C1—C4—N2	−179.01 (17)	C7—C6—N1—C1	−178.65 (14)
C2—C1—C4—N2	0.3 (3)	C1—C4—N2—N3	−0.3 (2)
C1—C2—C5—C6	0.09 (18)	C4—N2—N3—C3	0.2 (3)
C3—C2—C5—C6	−178.72 (17)	O1—C3—N3—N2	179.87 (16)
C1—C2—C5—C10	−179.86 (15)	C2—C3—N3—N2	−0.1 (2)
C3—C2—C5—C10	1.3 (3)	O2—C7—O3—C8	−1.8 (3)
C2—C5—C6—N1	−0.35 (18)	C6—C7—O3—C8	177.84 (15)
C10—C5—C6—N1	179.60 (15)	C9—C8—O3—C7	175.68 (16)
C2—C5—C6—C7	178.60 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1i	0.90 (3)	1.90 (3)	2.804 (2)	175 (2)
N1—H1···N2ii	0.86 (2)	2.08 (2)	2.925 (2)	166.2 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1i	0.90 (3)	1.90 (3)	2.804 (2)	175 (2)
N1—H1⋯N2ii	0.86 (2)	2.08 (2)	2.925 (2)	166.2 (17)

Symmetry codes: (i) ; (ii) .