Methyl 4-{[6-(4-bromo-phen-yl)-3-oxo-2,3,4,5-tetra-hydro-pyridazin-4-yl]methyl}benzoate.

The structure of the title compound, C(19)H(17)BrN(2)O(3), consists of two cyclic groups, viz. 4-(meth-oxy-carbon-yl)phenyl and 6-(4-bromo-phen-yl)-3-oxo-2,3,4,5-dihydro-pyridazin-4-yl, which are linked by a methyl-ene spacer. The pyridazine ring is twisted and the dihedral angle between its mean plane and that of the bromo-phenyl mean plane is 17.2 (2)°. The 4-(meth-oxy-carbon-yl)phenyl group shows a quasi-planar conformation, where the dihedral angle between the mean planes of the phenyl ring and carboxyl-ate ester group is 7.9 (4)°. Centrosymmetric inter-molecular N-H⋯O hydrogen bonds form dimers. These are linked by C-Br⋯O=C inter-actions [Br⋯O = 3.10 (1) Å] to form a one-dimensional polymeric structure running along the [1[Formula: see text]0] direction.

Related literature

For specific details concerning organic reactions and synthetic procedures for 4,5-diihydro-3(2H)-pyridazinone derivatives, see: Meyer et al. (2004 ▶). For the biological activity of heterocyclic compounds containing the 3(2H)-pyridazinone group, see: Sayed et al. (2002 ▶); Katrusiak & Baloniak (1994 ▶); Dogruer et al. (2003 ▶); Pieretti et al. (2006 ▶); Cao et al. (2003 ▶); Piaz et al. (1994 ▶); Xu et al. (2008 ▶); Giovannoni et al. (2007 ▶); Coelho et al. (2007 ▶); Malinka et al. (2003 ▶); Wexler et al. (1996 ▶); Barbaro et al., (2001 ▶); Vergelli et al. (2007 ▶); Abudshait (2007 ▶). For related structures, see: Zhang et al. (2006 ▶); Zhou & Zhou (2007 ▶). For C—Br⋯O inter­actions, see: Voronina et al. (2009 ▶)

Experimental

Crystal data

C19H17BrN2O3

M = 401.26

Triclinic,

a = 5.991 (1) Å

b = 8.958 (1) Å

c = 17.531 (2) Å

α = 99.502 (11)°

β = 95.241 (12)°

γ = 105.499 (10)°

V = 885.1 (2) Å3

Z = 2

Mo Kα radiation

μ = 2.34 mm−1

T = 293 K

0.50 × 0.33 × 0.13 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan [North et al. (1968 ▶) and PLATON (Spek, 2009 ▶)] T min = 0.567, T max = 0.978

3368 measured reflections

3151 independent reflections

2033 reflections with I > 2σ(I)

R int = 0.024

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.098

S = 1.03

3151 reflections

237 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.36 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: SET4 in CAD-4 Software; data reduction: HELENA (Spek, 1996 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681101467X/lw2061sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101467X/lw2061Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681101467X/lw2061Isup3.mol

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

C19H17BrN2O3	Z = 2
Mr = 401.26	F(000) = 408
Triclinic, P1	Dx = 1.506 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 5.991 (1) Å	Cell parameters from 25 reflections
b = 8.958 (1) Å	θ = 8.2–13.4°
c = 17.531 (2) Å	µ = 2.34 mm−1
α = 99.502 (11)°	T = 293 K
β = 95.241 (12)°	Block, colourless
γ = 105.499 (10)°	0.50 × 0.33 × 0.13 mm
V = 885.1 (2) Å3

Enraf–Nonius CAD-4 diffractometer	2033 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
graphite	θmax = 25.1°, θmin = 2.4°
ω/2θ scans	h = −7→6
Absorption correction: ψ scan [PLATON (Spek, 2009) and North et al. (1968)]	k = 0→10
Tmin = 0.567, Tmax = 0.978	l = −20→20
3368 measured reflections	3 standard reflections every 200 reflections
3151 independent reflections	intensity decay: 1%

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.047P)2 + 0.1645P] where P = (Fo2 + 2Fc2)/3
3151 reflections	(Δ/σ)max < 0.001
237 parameters	Δρmax = 0.28 e Å−3
4 restraints	Δρmin = −0.36 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br	−0.15083 (6)	−0.19522 (5)	0.35018 (3)	0.06171 (18)
O1	1.4961 (4)	0.5375 (3)	0.40556 (15)	0.0636 (7)
O2	0.7322 (7)	0.1015 (5)	−0.0912 (2)	0.1113 (14)
O3	0.5072 (5)	0.2549 (4)	−0.05798 (17)	0.0862 (10)
N2	0.9579 (5)	0.2989 (3)	0.44336 (17)	0.0477 (7)
N3	1.1821 (5)	0.4010 (3)	0.45053 (17)	0.0495 (7)
H3	1.2594	0.4324	0.4969	0.059*
C1	0.8308 (5)	0.2698 (4)	0.37748 (19)	0.0441 (9)
C4	1.2910 (6)	0.4559 (4)	0.3928 (2)	0.0478 (9)
C5	1.1519 (6)	0.4051 (6)	0.3128 (2)	0.0748 (13)
H5A	1.1718	0.3001	0.2959	0.090*	0.696 (16)
H5B	1.0661	0.4828	0.3257	0.090*	0.304 (16)
C6A	0.9009 (7)	0.3670 (12)	0.3173 (5)	0.053 (2)	0.696 (16)
H61A	0.8150	0.3097	0.2667	0.063*	0.696 (16)
H62A	0.8582	0.4644	0.3297	0.063*	0.696 (16)
C6B	0.936 (2)	0.2760 (19)	0.3030 (5)	0.049 (5)	0.304 (16)
H61B	0.9684	0.1765	0.2852	0.059*	0.304 (16)
H62B	0.8234	0.2891	0.2630	0.059*	0.304 (16)
C11	0.5908 (5)	0.1601 (4)	0.3696 (2)	0.0430 (8)
C12	0.4841 (6)	0.1357 (4)	0.4353 (2)	0.0485 (9)
H12	0.5620	0.1913	0.4843	0.058*
C13	0.2661 (6)	0.0313 (4)	0.4295 (2)	0.0505 (9)
H13	0.1970	0.0163	0.4741	0.061*
C14	0.1509 (5)	−0.0509 (4)	0.3570 (2)	0.0459 (9)
C15	0.2488 (6)	−0.0279 (4)	0.2906 (2)	0.0505 (9)
H15	0.1680	−0.0826	0.2418	0.061*
C16	0.4696 (6)	0.0776 (4)	0.2968 (2)	0.0489 (9)
H16	0.5370	0.0932	0.2520	0.059*
C20	1.2585 (6)	0.4905 (5)	0.2539 (2)	0.0636 (11)
H20A	1.4172	0.4836	0.2532	0.076*
H20B	1.2664	0.6013	0.2686	0.076*
C21	1.1228 (6)	0.4253 (5)	0.1732 (2)	0.0578 (10)
C22	1.1646 (7)	0.3022 (6)	0.1252 (3)	0.0761 (13)
H22	1.2879	0.2642	0.1408	0.091*
C23	1.0265 (8)	0.2329 (6)	0.0538 (3)	0.0768 (13)
H23	1.0584	0.1494	0.0220	0.092*
C24	0.8429 (7)	0.2863 (5)	0.0295 (2)	0.0592 (10)
C25	0.8033 (7)	0.4128 (5)	0.0761 (2)	0.0659 (11)
H25	0.6828	0.4528	0.0598	0.079*
C26	0.9426 (8)	0.4809 (5)	0.1475 (2)	0.0679 (12)
H26	0.9136	0.5663	0.1787	0.082*
C27	0.6928 (8)	0.2035 (6)	−0.0460 (3)	0.0723 (12)
C28	0.3469 (9)	0.1770 (7)	−0.1296 (3)	0.116 (2)
H28A	0.2053	0.2075	−0.1280	0.173*
H28B	0.3113	0.0645	−0.1344	0.173*
H28C	0.4184	0.2075	−0.1736	0.173*

	U11	U22	U33	U12	U13	U23
Br	0.0414 (2)	0.0561 (3)	0.0743 (3)	−0.00418 (16)	0.00693 (18)	0.00672 (19)
O1	0.0418 (14)	0.0744 (18)	0.0551 (17)	−0.0138 (13)	−0.0059 (12)	0.0156 (14)
O2	0.117 (3)	0.150 (3)	0.065 (2)	0.070 (3)	−0.010 (2)	−0.025 (2)
O3	0.080 (2)	0.117 (3)	0.058 (2)	0.046 (2)	−0.0112 (16)	−0.0057 (18)
N2	0.0352 (15)	0.0527 (18)	0.0452 (19)	0.0005 (13)	−0.0002 (14)	0.0052 (14)
N3	0.0373 (15)	0.0555 (18)	0.0426 (18)	−0.0010 (13)	−0.0034 (13)	0.0021 (15)
C1	0.0352 (18)	0.049 (2)	0.046 (2)	0.0084 (16)	0.0029 (17)	0.0105 (17)
C4	0.0378 (19)	0.052 (2)	0.046 (2)	0.0031 (16)	−0.0008 (17)	0.0083 (18)
C5	0.049 (2)	0.103 (3)	0.049 (3)	−0.016 (2)	−0.0062 (19)	0.021 (2)
C6A	0.041 (3)	0.051 (5)	0.060 (4)	−0.004 (3)	−0.004 (3)	0.027 (4)
C6B	0.051 (8)	0.041 (9)	0.045 (8)	−0.001 (7)	−0.003 (6)	0.010 (7)
C11	0.0337 (17)	0.047 (2)	0.046 (2)	0.0069 (15)	0.0014 (16)	0.0103 (17)
C12	0.0414 (19)	0.055 (2)	0.040 (2)	0.0050 (17)	0.0025 (16)	0.0011 (17)
C13	0.0406 (19)	0.055 (2)	0.051 (2)	0.0053 (17)	0.0113 (17)	0.0082 (19)
C14	0.0328 (17)	0.045 (2)	0.055 (2)	0.0027 (15)	0.0058 (16)	0.0088 (18)
C15	0.0422 (19)	0.054 (2)	0.044 (2)	0.0036 (17)	−0.0019 (17)	−0.0005 (18)
C16	0.0420 (19)	0.061 (2)	0.040 (2)	0.0066 (17)	0.0063 (16)	0.0113 (18)
C20	0.049 (2)	0.073 (3)	0.057 (3)	−0.005 (2)	0.0006 (19)	0.020 (2)
C21	0.045 (2)	0.071 (3)	0.050 (3)	−0.0007 (19)	0.0047 (19)	0.021 (2)
C22	0.059 (3)	0.111 (4)	0.064 (3)	0.035 (3)	0.006 (2)	0.017 (3)
C23	0.078 (3)	0.102 (4)	0.054 (3)	0.040 (3)	0.009 (2)	0.003 (3)
C24	0.060 (2)	0.078 (3)	0.042 (2)	0.022 (2)	0.0082 (19)	0.016 (2)
C25	0.070 (3)	0.071 (3)	0.056 (3)	0.024 (2)	−0.001 (2)	0.013 (2)
C26	0.082 (3)	0.062 (3)	0.053 (3)	0.016 (2)	−0.001 (2)	0.008 (2)
C27	0.079 (3)	0.095 (4)	0.044 (3)	0.031 (3)	0.009 (2)	0.009 (3)
C28	0.102 (4)	0.165 (6)	0.068 (4)	0.056 (4)	−0.028 (3)	−0.018 (4)

Br—C14	1.901 (3)	C12—C13	1.372 (5)
Br—O1i	3.096 (2)	C12—H12	0.9300
O1—C4	1.229 (4)	C13—C14	1.376 (5)
O2—C27	1.196 (5)	C13—H13	0.9300
O3—C27	1.325 (5)	C14—C15	1.372 (5)
O3—C28	1.456 (5)	C15—C16	1.388 (4)
N2—C1	1.271 (4)	C15—H15	0.9300
N2—N3	1.389 (4)	C16—H16	0.9300
N3—C4	1.343 (4)	C20—C21	1.505 (5)
N3—H3	0.8600	C20—H20A	0.9700
C1—C11	1.488 (4)	C20—H20B	0.9700
C1—C6A	1.495 (4)	C21—C22	1.366 (6)
C1—C6B	1.504 (5)	C21—C26	1.375 (6)
C4—C5	1.498 (5)	C22—C23	1.385 (6)
C5—C6B	1.462 (5)	C22—H22	0.9300
C5—C6A	1.463 (4)	C23—C24	1.373 (5)
C5—C20	1.477 (5)	C23—H23	0.9300
C5—H5A	0.9800	C24—C25	1.371 (6)
C5—H5B	0.9800	C24—C27	1.487 (6)
C6A—H5B	1.2052	C25—C26	1.386 (6)
C6A—H61A	0.9700	C25—H25	0.9300
C6A—H62A	0.9700	C26—H26	0.9300
C6B—H61B	0.9700	C28—H28A	0.9600
C6B—H62B	0.9700	C28—H28B	0.9600
C11—C12	1.388 (5)	C28—H28C	0.9600
C11—C16	1.391 (5)
C14—Br—O1i	152.32 (12)	C12—C13—C14	119.2 (3)
C27—O3—C28	116.1 (4)	C12—C13—H13	120.4
C1—N2—N3	116.8 (3)	C14—C13—H13	120.4
C4—N3—N2	127.0 (3)	C15—C14—C13	121.0 (3)
C4—N3—H3	116.5	C15—C14—Br	120.3 (3)
N2—N3—H3	116.5	C13—C14—Br	118.7 (3)
N2—C1—C11	116.9 (3)	C14—C15—C16	119.4 (3)
N2—C1—C6A	120.7 (4)	C14—C15—H15	120.3
C11—C1—C6A	121.2 (3)	C16—C15—H15	120.3
N2—C1—C6B	121.5 (7)	C15—C16—C11	120.5 (3)
C11—C1—C6B	115.6 (4)	C15—C16—H16	119.7
O1—C4—N3	121.0 (3)	C11—C16—H16	119.7
O1—C4—C5	122.8 (3)	C5—C20—C21	112.3 (3)
N3—C4—C5	116.1 (3)	C5—C20—H20A	109.1
C6B—C5—C20	129.0 (5)	C21—C20—H20A	109.1
C6A—C5—C20	122.3 (4)	C5—C20—H20B	109.1
C6B—C5—C4	116.4 (6)	C21—C20—H20B	109.1
C6A—C5—C4	110.8 (4)	H20A—C20—H20B	107.9
C20—C5—C4	114.6 (3)	C22—C21—C26	117.9 (4)
C6A—C5—H5A	101.8	C22—C21—C20	121.1 (4)
C20—C5—H5A	101.8	C26—C21—C20	120.9 (4)
C4—C5—H5A	101.8	C21—C22—C23	121.2 (4)
C6B—C5—H5B	90.6	C21—C22—H22	119.4
C20—C5—H5B	90.6	C23—C22—H22	119.4
C4—C5—H5B	90.6	C24—C23—C22	120.6 (4)
H5A—C5—H5B	156.6	C24—C23—H23	119.7
C5—C6A—C1	112.7 (4)	C22—C23—H23	119.7
C1—C6A—H5B	126.3	C25—C24—C23	118.8 (4)
C5—C6A—H61A	109.1	C25—C24—C27	122.6 (4)
C1—C6A—H61A	109.1	C23—C24—C27	118.7 (4)
H5B—C6A—H61A	123.3	C24—C25—C26	120.0 (4)
C5—C6A—H62A	109.1	C24—C25—H25	120.0
C1—C6A—H62A	109.1	C26—C25—H25	120.0
H61A—C6A—H62A	107.8	C21—C26—C25	121.5 (4)
C5—C6B—C1	112.2 (5)	C21—C26—H26	119.2
C5—C6B—H61B	109.2	C25—C26—H26	119.2
C1—C6B—H61B	109.2	O2—C27—O3	123.1 (4)
C5—C6B—H62B	109.2	O2—C27—C24	124.5 (4)
C1—C6B—H62B	109.2	O3—C27—C24	112.4 (4)
H61B—C6B—H62B	107.9	O3—C28—H28A	109.5
C12—C11—C16	118.3 (3)	O3—C28—H28B	109.5
C12—C11—C1	120.5 (3)	H28A—C28—H28B	109.5
C16—C11—C1	121.2 (3)	O3—C28—H28C	109.5
C13—C12—C11	121.4 (3)	H28A—C28—H28C	109.5
C13—C12—H12	119.3	H28B—C28—H28C	109.5
C11—C12—H12	119.3
C1—N2—N3—C4	−9.7 (5)	C12—C13—C14—Br	179.9 (3)
N3—N2—C1—C11	179.8 (3)	O1i—Br—C14—C15	137.0 (3)
N3—N2—C1—C6A	−12.7 (6)	O1i—Br—C14—C13	−44.1 (5)
N3—N2—C1—C6B	28.2 (10)	C13—C14—C15—C16	1.3 (6)
N2—N3—C4—O1	−175.0 (3)	Br—C14—C15—C16	−179.8 (3)
N2—N3—C4—C5	2.1 (6)	C14—C15—C16—C11	−0.3 (6)
O1—C4—C5—C6B	164.1 (11)	C12—C11—C16—C15	−0.8 (5)
N3—C4—C5—C6B	−13.0 (11)	C1—C11—C16—C15	178.0 (3)
O1—C4—C5—C6A	−157.3 (5)	C6B—C5—C20—C21	−2.8 (14)
N3—C4—C5—C6A	25.7 (6)	C6A—C5—C20—C21	−46.4 (8)
O1—C4—C5—C20	−14.0 (6)	C4—C5—C20—C21	174.9 (4)
N3—C4—C5—C20	168.9 (4)	C5—C20—C21—C22	−87.0 (5)
C20—C5—C6A—C1	175.7 (5)	C5—C20—C21—C26	88.7 (5)
C4—C5—C6A—C1	−44.3 (9)	C26—C21—C22—C23	−1.5 (6)
N2—C1—C6A—C5	40.7 (10)	C20—C21—C22—C23	174.3 (4)
C11—C1—C6A—C5	−152.3 (5)	C21—C22—C23—C24	−0.2 (7)
C20—C5—C6B—C1	−154.1 (8)	C22—C23—C24—C25	2.0 (7)
C4—C5—C6B—C1	28.1 (19)	C22—C23—C24—C27	−177.2 (4)
N2—C1—C6B—C5	−38.1 (19)	C23—C24—C25—C26	−2.1 (6)
C11—C1—C6B—C5	169.9 (10)	C27—C24—C25—C26	177.1 (4)
N2—C1—C11—C12	21.7 (5)	C22—C21—C26—C25	1.5 (6)
C6A—C1—C11—C12	−145.8 (6)	C20—C21—C26—C25	−174.3 (4)
C6B—C1—C11—C12	175.0 (11)	C24—C25—C26—C21	0.3 (7)
N2—C1—C11—C16	−157.2 (4)	C28—O3—C27—O2	1.4 (7)
C6A—C1—C11—C16	35.4 (7)	C28—O3—C27—C24	−178.3 (4)
C6B—C1—C11—C16	−3.8 (11)	C25—C24—C27—O2	173.6 (5)
C16—C11—C12—C13	1.0 (5)	C23—C24—C27—O2	−7.2 (7)
C1—C11—C12—C13	−177.9 (3)	C25—C24—C27—O3	−6.6 (6)
C11—C12—C13—C14	0.0 (6)	C23—C24—C27—O3	172.6 (4)
C12—C13—C14—C15	−1.2 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1ii	0.86	2.08	2.910 (4)	162
C14—Br···O1i	1.901 (3)	3.096 (2)	?	152.32 (12)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1i	0.86	2.08	2.910 (4)	162

Symmetry codes: (i) ; (ii) .