3-(4-Bromo-phen-yl)-4-[2-(4-nitro-phen-yl)hydrazin-yl]furan-2(5H)-one.

In the title compound, C(16)H(12)BrN(3)O(4), the furan-2(5H)-one ring forms a dihedral angle of 33.19 (9)° with the 4-bromo-benzene unit and is nearly perpendicular to the 4-nitro-benzene segment, making a dihedral angle of 89.93 (10)°. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules, generating an infinite chain along [010]. The chains are linked into a three-dimensional network by C-H⋯O, C-H⋯π and π-π contacts [centroid-centroid separation = 3.805 (2) Å].

Related literature

For background to 3-aryl­furan-2(5H)-ones as anti­bacterial agents, see: Xiao et al. (2011a ▶, ▶). For further details of C—H⋯π inter­actions, see: Castillo et al. (2009 ▶); Li et al. (2007 ▶); Trilleras et al. (2009 ▶).

Experimental

Crystal data

C16H12BrN3O4

M = 390.20

Orthorhombic,

a = 14.4725 (11) Å

b = 6.7744 (5) Å

c = 31.310 (2) Å

V = 3069.8 (4) Å3

Z = 8

Mo Kα radiation

μ = 2.71 mm−1

T = 296 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.498, T max = 0.614

16108 measured reflections

3022 independent reflections

2039 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.096

S = 1.02

3022 reflections

224 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.58 e Å−3

Δρmin = −0.63 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811043947/hb6467sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043947/hb6467Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811043947/hb6467Isup3.cml

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

C16H12BrN3O4	F(000) = 1568
Mr = 390.20	Dx = 1.689 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1957 reflections
a = 14.4725 (11) Å	θ = 2.3–24.6°
b = 6.7744 (5) Å	µ = 2.71 mm−1
c = 31.310 (2) Å	T = 296 K
V = 3069.8 (4) Å3	Block, colorless
Z = 8	0.30 × 0.20 × 0.20 mm

Bruker SMART APEX CCD diffractometer	3022 independent reflections
Radiation source: fine-focus sealed tube	2039 reflections with I > 2σ(I)
graphite	Rint = 0.046
φ and ω scan	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→17
Tmin = 0.498, Tmax = 0.614	k = −8→7
16108 measured reflections	l = −38→35

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0432P)2 + 1.6464P] where P = (Fo2 + 2Fc2)/3
3022 reflections	(Δ/σ)max = 0.001
224 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.63 e Å−3

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
Br1	0.61747 (3)	0.27111 (6)	0.394041 (10)	0.05931 (16)
C1	0.62850 (19)	0.4835 (4)	0.53598 (9)	0.0311 (6)
C2	0.6776 (2)	0.5813 (5)	0.50422 (10)	0.0429 (8)
H2	0.7131	0.6909	0.5114	0.051*
C3	0.6746 (2)	0.5187 (5)	0.46235 (10)	0.0452 (8)
H3A	0.7078	0.5851	0.4414	0.054*
C4	0.6220 (2)	0.3580 (5)	0.45199 (9)	0.0390 (7)
C5	0.5723 (2)	0.2560 (4)	0.48239 (9)	0.0407 (7)
H5	0.5371	0.1465	0.4749	0.049*
C6	0.5761 (2)	0.3203 (4)	0.52416 (9)	0.0361 (7)
H6	0.5427	0.2529	0.5449	0.043*
C7	0.63070 (19)	0.5525 (4)	0.58069 (9)	0.0316 (6)
C8	0.6358 (2)	0.7596 (4)	0.59231 (10)	0.0389 (7)
C9	0.6233 (2)	0.5875 (4)	0.65466 (9)	0.0407 (7)
H9A	0.5653	0.5791	0.6701	0.049*
H9B	0.6736	0.5581	0.6741	0.049*
C10	0.62402 (19)	0.4491 (4)	0.61743 (9)	0.0329 (7)
C11	0.5150 (2)	0.1371 (4)	0.67875 (9)	0.0326 (7)
C12	0.5037 (2)	0.0240 (4)	0.71579 (9)	0.0368 (7)
H12	0.5552	−0.0264	0.7298	0.044*
C13	0.4173 (2)	−0.0127 (4)	0.73158 (9)	0.0383 (7)
H13	0.4098	−0.0871	0.7563	0.046*
C14	0.3413 (2)	0.0617 (4)	0.71039 (9)	0.0352 (7)
C15	0.3506 (2)	0.1675 (5)	0.67330 (9)	0.0399 (7)
H15	0.2986	0.2133	0.6589	0.048*
C16	0.4374 (2)	0.2055 (4)	0.65750 (9)	0.0396 (7)
H16	0.4441	0.2774	0.6324	0.048*
H2A	0.649 (2)	0.101 (5)	0.6741 (11)	0.057 (11)*
N1	0.61816 (19)	0.2544 (4)	0.62466 (9)	0.0414 (6)
N2	0.60423 (18)	0.1894 (4)	0.66655 (8)	0.0368 (6)
N3	0.24976 (19)	0.0297 (4)	0.72818 (8)	0.0421 (6)
O1	0.63888 (16)	0.9067 (3)	0.57072 (7)	0.0497 (6)
O2	0.63469 (16)	0.7778 (3)	0.63613 (7)	0.0464 (6)
O3	0.24263 (16)	−0.0574 (3)	0.76267 (7)	0.0525 (6)
O4	0.18281 (16)	0.0904 (4)	0.70812 (8)	0.0560 (6)
H1A	0.627 (2)	0.175 (6)	0.6061 (11)	0.056*

	U11	U22	U33	U12	U13	U23
Br1	0.0609 (3)	0.0811 (3)	0.0360 (2)	0.0105 (2)	−0.00079 (16)	−0.01532 (18)
C1	0.0306 (15)	0.0285 (15)	0.0342 (15)	0.0027 (13)	0.0037 (12)	0.0014 (12)
C2	0.0419 (18)	0.0435 (19)	0.0432 (18)	−0.0119 (15)	0.0059 (15)	−0.0043 (15)
C3	0.046 (2)	0.052 (2)	0.0378 (17)	−0.0066 (17)	0.0116 (15)	0.0034 (16)
C4	0.0411 (18)	0.0452 (19)	0.0308 (16)	0.0082 (15)	−0.0015 (14)	−0.0065 (14)
C5	0.0483 (19)	0.0339 (17)	0.0399 (17)	−0.0005 (15)	−0.0026 (14)	−0.0024 (15)
C6	0.0403 (18)	0.0313 (16)	0.0367 (16)	−0.0026 (14)	0.0049 (13)	0.0014 (13)
C7	0.0353 (16)	0.0270 (15)	0.0324 (15)	−0.0005 (12)	0.0044 (13)	−0.0015 (12)
C8	0.0439 (18)	0.0331 (18)	0.0398 (17)	−0.0002 (14)	0.0019 (13)	−0.0024 (15)
C9	0.056 (2)	0.0332 (17)	0.0332 (16)	−0.0017 (15)	0.0021 (14)	−0.0028 (13)
C10	0.0310 (15)	0.0302 (16)	0.0373 (16)	−0.0018 (12)	0.0035 (13)	−0.0052 (12)
C11	0.0422 (17)	0.0234 (14)	0.0321 (15)	0.0007 (13)	−0.0022 (13)	−0.0043 (12)
C12	0.0414 (18)	0.0335 (17)	0.0356 (16)	0.0032 (13)	−0.0064 (14)	0.0046 (14)
C13	0.0475 (19)	0.0344 (17)	0.0331 (16)	−0.0005 (14)	0.0004 (14)	0.0046 (13)
C14	0.0371 (17)	0.0340 (17)	0.0346 (16)	−0.0010 (13)	0.0005 (13)	−0.0043 (13)
C15	0.0419 (18)	0.0434 (18)	0.0343 (16)	0.0065 (14)	−0.0102 (14)	−0.0022 (14)
C16	0.053 (2)	0.0349 (17)	0.0310 (15)	0.0034 (15)	−0.0035 (14)	0.0033 (13)
N1	0.0598 (17)	0.0287 (15)	0.0357 (14)	−0.0025 (13)	0.0105 (13)	−0.0037 (11)
N2	0.0429 (16)	0.0332 (14)	0.0343 (14)	0.0002 (12)	0.0031 (12)	0.0036 (12)
N3	0.0442 (16)	0.0362 (15)	0.0458 (15)	0.0023 (12)	−0.0006 (14)	−0.0066 (13)
O1	0.0742 (17)	0.0283 (12)	0.0466 (13)	−0.0027 (11)	0.0062 (12)	0.0009 (10)
O2	0.0715 (16)	0.0289 (12)	0.0389 (12)	−0.0033 (11)	0.0000 (11)	−0.0082 (9)
O3	0.0493 (14)	0.0603 (15)	0.0478 (14)	−0.0014 (12)	0.0069 (11)	0.0025 (12)
O4	0.0396 (13)	0.0637 (16)	0.0648 (15)	0.0070 (12)	−0.0068 (12)	−0.0035 (13)

Br1—C4	1.909 (3)	C9—H9B	0.9700
C1—C2	1.390 (4)	C10—N1	1.341 (4)
C1—C6	1.391 (4)	C11—C16	1.385 (4)
C1—C7	1.476 (4)	C11—N2	1.393 (4)
C2—C3	1.379 (4)	C11—C12	1.399 (4)
C2—H2	0.9300	C12—C13	1.368 (4)
C3—C4	1.368 (4)	C12—H12	0.9300
C3—H3A	0.9300	C13—C14	1.380 (4)
C4—C5	1.378 (4)	C13—H13	0.9300
C5—C6	1.380 (4)	C14—C15	1.371 (4)
C5—H5	0.9300	C14—N3	1.453 (4)
C6—H6	0.9300	C15—C16	1.374 (4)
C7—C10	1.350 (4)	C15—H15	0.9300
C7—C8	1.451 (4)	C16—H16	0.9300
C8—O1	1.205 (3)	N1—N2	1.398 (4)
C8—O2	1.378 (4)	N1—H1A	0.80 (4)
C9—O2	1.423 (4)	N2—H2A	0.91 (3)
C9—C10	1.496 (4)	N3—O4	1.226 (3)
C9—H9A	0.9700	N3—O3	1.235 (3)
C2—C1—C6	117.9 (3)	N1—C10—C9	119.0 (3)
C2—C1—C7	121.1 (3)	C7—C10—C9	109.8 (2)
C6—C1—C7	121.1 (3)	C16—C11—N2	122.3 (3)
C3—C2—C1	121.2 (3)	C16—C11—C12	119.1 (3)
C3—C2—H2	119.4	N2—C11—C12	118.3 (3)
C1—C2—H2	119.4	C13—C12—C11	120.4 (3)
C4—C3—C2	119.2 (3)	C13—C12—H12	119.8
C4—C3—H3A	120.4	C11—C12—H12	119.8
C2—C3—H3A	120.4	C12—C13—C14	119.2 (3)
C3—C4—C5	121.7 (3)	C12—C13—H13	120.4
C3—C4—Br1	119.3 (2)	C14—C13—H13	120.4
C5—C4—Br1	118.9 (2)	C15—C14—C13	121.3 (3)
C4—C5—C6	118.4 (3)	C15—C14—N3	119.5 (3)
C4—C5—H5	120.8	C13—C14—N3	119.2 (3)
C6—C5—H5	120.8	C14—C15—C16	119.5 (3)
C5—C6—C1	121.7 (3)	C14—C15—H15	120.2
C5—C6—H6	119.2	C16—C15—H15	120.2
C1—C6—H6	119.2	C15—C16—C11	120.4 (3)
C10—C7—C8	107.0 (3)	C15—C16—H16	119.8
C10—C7—C1	129.9 (3)	C11—C16—H16	119.8
C8—C7—C1	123.0 (3)	C10—N1—N2	118.5 (3)
O1—C8—O2	119.0 (3)	C10—N1—H1A	122 (3)
O1—C8—C7	131.4 (3)	N2—N1—H1A	119 (3)
O2—C8—C7	109.6 (3)	C11—N2—N1	118.1 (2)
O2—C9—C10	104.4 (2)	C11—N2—H2A	115 (2)
O2—C9—H9A	110.9	N1—N2—H2A	110 (2)
C10—C9—H9A	110.9	O4—N3—O3	122.8 (3)
O2—C9—H9B	110.9	O4—N3—C14	118.3 (3)
C10—C9—H9B	110.9	O3—N3—C14	118.9 (3)
H9A—C9—H9B	108.9	C8—O2—C9	109.0 (2)
N1—C10—C7	131.2 (3)
C6—C1—C2—C3	−0.1 (5)	O2—C9—C10—C7	−2.7 (3)
C7—C1—C2—C3	−179.1 (3)	C16—C11—C12—C13	−2.2 (4)
C1—C2—C3—C4	0.2 (5)	N2—C11—C12—C13	172.9 (3)
C2—C3—C4—C5	−0.3 (5)	C11—C12—C13—C14	0.5 (4)
C2—C3—C4—Br1	179.9 (2)	C12—C13—C14—C15	1.6 (5)
C3—C4—C5—C6	0.3 (5)	C12—C13—C14—N3	−177.4 (3)
Br1—C4—C5—C6	−179.9 (2)	C13—C14—C15—C16	−1.9 (4)
C4—C5—C6—C1	−0.1 (5)	N3—C14—C15—C16	177.1 (3)
C2—C1—C6—C5	0.0 (4)	C14—C15—C16—C11	0.1 (4)
C7—C1—C6—C5	179.0 (3)	N2—C11—C16—C15	−173.0 (3)
C2—C1—C7—C10	−148.8 (3)	C12—C11—C16—C15	1.9 (4)
C6—C1—C7—C10	32.2 (5)	C7—C10—N1—N2	−174.8 (3)
C2—C1—C7—C8	34.9 (4)	C9—C10—N1—N2	5.0 (4)
C6—C1—C7—C8	−144.0 (3)	C16—C11—N2—N1	−21.9 (4)
C10—C7—C8—O1	−176.9 (3)	C12—C11—N2—N1	163.1 (2)
C1—C7—C8—O1	0.1 (5)	C10—N1—N2—C11	99.7 (3)
C10—C7—C8—O2	1.7 (3)	C15—C14—N3—O4	3.7 (4)
C1—C7—C8—O2	178.7 (3)	C13—C14—N3—O4	−177.3 (3)
C8—C7—C10—N1	−179.4 (3)	C15—C14—N3—O3	−176.5 (3)
C1—C7—C10—N1	3.8 (5)	C13—C14—N3—O3	2.6 (4)
C8—C7—C10—C9	0.7 (3)	O1—C8—O2—C9	175.3 (3)
C1—C7—C10—C9	−176.0 (3)	C7—C8—O2—C9	−3.5 (3)
O2—C9—C10—N1	177.4 (3)	C10—C9—O2—C8	3.7 (3)

Cg3 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.80 (4)	2.13 (4)	2.913 (3)	163 (4)
N2—H2A···O2i	0.91 (3)	2.50 (3)	2.979 (3)	113 (2)
C9—H9B···O3ii	0.97	2.45	3.380 (4)	161
C2—H2···Cg3iii	0.93	2.86	3.676 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.80 (4)	2.13 (4)	2.913 (3)	163 (4)
N2—H2A⋯O2i	0.91 (3)	2.50 (3)	2.979 (3)	113 (2)
C9—H9B⋯O3ii	0.97	2.45	3.380 (4)	161
C2—H2⋯Cg3iii	0.93	2.86	3.676 (3)	147

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