Methyl 4-{[6-(4-bromo­phen­yl)-3-oxo-2,3,4,5-tetra­hydro­pyridazin-4-yl]methyl}benzoate

Bortoluzzi, A.J.; Souza, L.B.P.; Joussef, A.C.; Meyer, E.

doi:10.1107/S160053681101467X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Pages o1230-o1231

doi:10.1107/S160053681101467X

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Methyl 4-{[6-(4-bromophenyl)-3-oxo-2,3,4,5-tetrahydropyridazin-4-yl]methyl}benzoate

Adailton J. Bortoluzzi,^a ^* Luciana B. P. Souza,^a Antônio C. Joussef ^a and Emerson Meyer ^b

^aDepartamento de Química, UFSC, 88040-900 Florianópolis, SC, Brazil, and ^bDepartamento de Química, UEM, 87020-900 Maringá, PR, Brazil
^*Correspondence e-mail: adajb@qmc.ufsc.br

(Received 13 April 2011; accepted 19 April 2011; online 29 April 2011)

The structure of the title compound, C₁₉H₁₇BrN₂O₃, consists of two cyclic groups, viz. 4-(methoxycarbonyl)phenyl and 6-(4-bromophenyl)-3-oxo-2,3,4,5-dihydropyridazin-4-yl, which are linked by a methylene spacer. The pyridazine ring is twisted and the dihedral angle between its mean plane and that of the bromophenyl mean plane is 17.2 (2)°. The 4-(methoxycarbonyl)phenyl group shows a quasi-planar conformation, where the dihedral angle between the mean planes of the phenyl ring and carboxylate ester group is 7.9 (4)°. Centrosymmetric intermolecular N—H⋯O hydrogen bonds form dimers. These are linked by C—Br⋯O=C interactions [Br⋯O = 3.10 (1) Å] to form a one-dimensional polymeric structure running along the [1 $[\overline{2}]$ 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_r = 401.26
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.038
wR(F²) = 0.098
S = 1.03
3151 reflections
237 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.36 e Å⁻³

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) -x+3, -y+1, -z+1; (ii) x-2, y-1, z.

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.

Supporting information

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

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

Supporting information file. DOI: 10.1107/S160053681101467X/lw2061Isup3.mol

checkCIF report

Comment top

Heterocyclic compounds containing 3-(2H)-pyridazinone moiety in their structures have attracted a great deal of attention due to their wide spectrum of biological activity such as antimicrobial (Sayed et al., 2002; Katrusiak & Baloniak, 1994), anti-inflammatory (Dogruer et al., 2003; Pieretti et al., 2006), antifeedant (Cao et al., 2003), herbicidal (Piaz et al., 1994; Xu et al., 2008), antiplatelet (Giovannoni et al., 2007; Coelho et al., 2007), anticancer (Malinka et al., 2003), antihypertensive (Wexler et al., 1996; Barbaro et al., 2001), antinociceptive agent (Giovannoni et al., 2007; Vergelli et al., 2007) and other biological and pharmacological properties (Abudshait, 2007). In our study toward the synthesis of dihydropyridazinones as potential candidates for antihypertensive activity the structure of methyl 4-[6-(4-bromophenyl)-3-oxo-2,3,4,5-dihydropyridazin-4-ylmethyl]benzoate has been determined.

The structure of the title compound consists of two cyclic moieties, 4-(methoxycarbonyl)phenyl and 6-(4-bromophenyl)-3-oxo-2,3,4,5-dihydropyridazin-4-yl, which are linked by methylene spacer (Fig. 1). The pyridazinyl ring is twisted, the greatest deviation is observed for carbon atoms C5 and the disordered C6A and C6B atoms, which are -0.0674 (8), 0.479 (5) and -0.415 (12) Å, respectively, out of the mean plane of all atoms in the ring. The dihedral angle between the mean plane of this ring and that of the bromophenyl mean plane is 17.2 (2)°. The 4-(Methoxycarbonyl)phenyl moiety shows quasi-planar conformation, where the dihedral angle between the mean planes of the phenyl ring and carboxylate ester group is 7.9 (4)°. Intermolecular N3—H3N···O1 hydrogen bonds form centrosymmetric dimers (Fig. 2). Each dimer is linked to two neighboring dimers through C4═O1···Br—C14 interactions (Voronina et al., 2009) forming an one-dimensional polymeric structure along [120] direction (Fig. 3). In addition, packing analysis shows that the molecules are perfectly stacked along [100] direction (Fig. 4).

Related literature top

For specific details concerning organic reactions and synthetic procedures for 4,5-diihydro-3(2H)-pyridazinone derivatives, see: Meyer et al. (2004). For biological activity, 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 top

The title compound was synthesized according to a previously described method (Meyer et al., 2004). A careful crystallization from methanol/water (1:1 v/v) provided colorless crystals suitable for X-ray analysis.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: SET4 in CAD-4 Software (Enraf–Nonius, 1989); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of title compound showing the atom-labelling scheme. Ellipsoids are drawn at the 50% probability level.
	Fig. 2. Dimeric structure formed by hydrogen bonds. Symmetry code: -x + 3, -y + 1, -z + 1
	Fig. 3. One-dimensional polymeric structure formed by C—Br···O=C interactions. Symmetry code: -2 + x, -1 + y, z
	Fig. 4. Packing showing the molecules staked along [100] direction.

Methyl 4-{[6-(4-bromophenyl)-3-oxo-2,3,4,5-tetrahydropyridazin-4-yl]methyl}benzoate top

Crystal data top

C₁₉H₁₇BrN₂O₃	Z = 2
M_r = 401.26	F(000) = 408
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.047P)² + 0.1645P] where P = (F_o² + 2F_c²)/3
3151 reflections	(Δ/σ)_max < 0.001
237 parameters	Δρ_max = 0.28 e Å⁻³
4 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₉H₁₇BrN₂O₃	γ = 105.499 (10)°
M_r = 401.26	V = 885.1 (2) Å³
Triclinic, P1	Z = 2
a = 5.991 (1) Å	Mo Kα radiation
b = 8.958 (1) Å	µ = 2.34 mm⁻¹
c = 17.531 (2) Å	T = 293 K
α = 99.502 (11)°	0.50 × 0.33 × 0.13 mm
β = 95.241 (12)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2033 reflections with I > 2σ(I)
Absorption correction: ψ scan [PLATON (Spek, 2009) and North et al. (1968)]	R_int = 0.024
T_min = 0.567, T_max = 0.978	3 standard reflections every 200 reflections
3368 measured reflections	intensity decay: 1%
3151 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	4 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.03	Δρ_max = 0.28 e Å⁻³
3151 reflections	Δρ_min = −0.36 e Å⁻³
237 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) x−2, y−1, z.

Hydrogen-bond geometry (Å, º) top

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	1.90 (1)	3.10 (1)	?	152 (1)

Symmetry codes: (i) x−2, y−1, z; (ii) −x+3, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₇BrN₂O₃
M_r	401.26
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	5.991 (1), 8.958 (1), 17.531 (2)
α, β, γ (°)	99.502 (11), 95.241 (12), 105.499 (10)
V (Å³)	885.1 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.34
Crystal size (mm)	0.50 × 0.33 × 0.13

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan [PLATON (Spek, 2009) and North et al. (1968)]
T_min, T_max	0.567, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	3368, 3151, 2033
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.098, 1.03
No. of reflections	3151
No. of parameters	237
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.36

Computer programs: , SET4 in CAD-4 Software (Enraf–Nonius, 1989), HELENA (Spek, 1996), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x+3, −y+1, −z+1; (ii) x−2, y−1, z.

Acknowledgements

The authors thank the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES), the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) and the Financiadora de Estudos e Projetos (FINEP) for financial support.

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Volume 67| Part 5| May 2011| Pages o1230-o1231

doi:10.1107/S160053681101467X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Methyl 4-{[6-(4-bromo­phen­yl)-3-oxo-2,3,4,5-tetra­hydro­pyridazin-4-yl]methyl}benzoate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Methyl 4-{[6-(4-bromophenyl)-3-oxo-2,3,4,5-tetrahydropyridazin-4-yl]methyl}benzoate