3-(4-Bromo­phen­yl)-4-[2-(4-nitro­phen­yl)hydrazin­yl]furan-2(5H)-one

Xiao, Z.-P.; Yi, L.-C.; Li, J.-L.; Zhang, B.; Liao, M.-L.

doi:10.1107/S1600536811043947

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3086

doi:10.1107/S1600536811043947

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3-(4-Bromophenyl)-4-[2-(4-nitrophenyl)hydrazinyl]furan-2(5H)-one

Zhu-Ping Xiao,^a ^* Li-Cheng Yi,^a Jia-Liang Li,^a Bo Zhang ^a and Mei-Ling Liao ^a

^aCollege of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, People's Republic of China
^*Correspondence e-mail: xiaozhuping2005@163.com

(Received 20 October 2011; accepted 23 October 2011; online 29 October 2011)

In the title compound, C₁₆H₁₂BrN₃O₄, the furan-2(5H)-one ring forms a dihedral angle of 33.19 (9)° with the 4-bromobenzene unit and is nearly perpendicular to the 4-nitrobenzene segment, making a dihedral angle of 89.93 (10)°. In the crystal, N—H⋯O hydrogen bonds link the molecules, 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 ,b ,c). 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_r = 390.20
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.036
wR(F²) = 0.096
S = 1.02
3022 reflections
224 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.63 e Å⁻³

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) x, y-1, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811043947/hb6467sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811043947/hb6467Isup3.cml

checkCIF report

Comment top

Furan-2(5H)-one framework is a part of many natural and synthetic compounds, which possess useful biological activities including anti-inflammatory and antitumor activity. Recently, we demostrated that 3-arylfuran-2(5H)-ones as antibacterial agent, some of which are potent tyrosyl t-RNA synthase inhibitors (Xiao et al., 2011a, 2011b and 2011c). Herein, we reported the crystal structure of the title compound (I) (Fig. 1).

The bond length of C7—C10 is 1.350 (4) Å and was assigned as a double bond, and the title compound was therefore identified as a furan-2(5H)-one (scheme 1). The torsion angle of N2—N1—C10—C7 is 174.8 (3) °, indicating that N1 may adopt sp² hybridization. Therefore the p orbital of N1 is conjugated with the π molecular orbital of C7—C10 double bond, which shortens the N1—C10 bond from 1.48 Å to 1.341 (4) Å. However, the torsion angle of N1—N2—C11—C16 is 21.9 (4), indicating that N2 is unlikely to have sp² hybridization. In fact, the angle of C11—N2—H2A, C11—N2—N1 and N1—N2—H2A are 114.83 (184), 110.30 (216) and 118.11 (24), respectively. These angles are in the range of 108 to 120 °, indicating that N2 may show a type of hybridization between sp² and sp³. This resulted in a decrease of the overlap between the nitrogen (N2) and the benzene π-orbital and elongates the N2—C11 bond (1.393 (4) Å) in comparsion with N1—C10.

In the extended structure of I, a line of molecules is generated along the b axis through N1—H1A···O1 and N2—H2A···O2 hydrogen bonds characterized by a graph-set motif of R₂²(7) (Fig. 2). Utilizing the oxygen in the nitro group as acceptor, C—H···O hydrogen bonds link pairs of the resulted lines into centrosymmetric dimers, which are generated by edge fused graph-set motifs of R₃³(23) (Fig.2).

Adjacent dimeric lines are linked together via C2—H2···π contacts, forming an infinite two-dimensional layer parallel to the plane (001). The H···π length of the typical C—H···π hydrogen bond is in the range of 2.70 to 3.10 Å (Trilleras et al., 2009; Castillo, et al., 2009; Li, et al., 2007). C2—H2···π in compound I is thus considerated as a moderate contact with H···Cg length of 2.86 Å, where Cg is the centroid of C1 to C6 (Fig. 3). The resulted layers lie parallel to the plane (001), which are further linked to form its final three-dimensional network through π–π interactions with center-center length of 3.805 (2) Å (Fig. 4).

Related literature top

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

Experimental top

3-(4-Bromophenyl)-4-hydroxyfuran-2(5H)-one (0.51 g, 2 mmol) was added to a mixture of 4-nitrophenylhydrazine (0.37 g, 2.4 mmol) and p-toluene sulphonic acid (13.6 mg, 0.08 mmol). The resulted mixture was heated to 375 K for 30 min. Fifteen ml of toluene was then added and refluxed for 7 h. After toluene was removed under reduced pressure, the residue was purified by column chromatography on silica gel, eluting with EtOAc/petroleum ether (v/v = 2/1), which was partially evaporated to give colorless blocks of (I).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. A dimeric line is formed through intermolecular N—H···O and C—H···O hydrogen bonds. For the sake of clarity, the H atoms have been omitted except that involving in hydrogen bonds.
	Fig. 3. A two-dimensional layer is generated through intermolecular C—H···π contacts. For the sake of clarity, the H atoms have been omitted except that involving in hydrogen bonds.
	Fig. 4. A three-dimensional network is finally formed through π–π interactions. For the sake of clarity, the H atoms have been omitted except that involving in hydrogen bonds.

3-(4-Bromophenyl)-4-[2-(4-nitrophenyl)hydrazinyl]furan-2(5H)-one top

Crystal data top

C₁₆H₁₂BrN₃O₄	F(000) = 1568
M_r = 390.20	D_x = 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

Data collection top

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

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)] = 0.036	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(F_o²) + (0.0432P)² + 1.6464P] where P = (F_o² + 2F_c²)/3
3022 reflections	(Δ/σ)_max = 0.001
224 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

C₁₆H₁₂BrN₃O₄	V = 3069.8 (4) Å³
M_r = 390.20	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 14.4725 (11) Å	µ = 2.71 mm⁻¹
b = 6.7744 (5) Å	T = 296 K
c = 31.310 (2) Å	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker SMART APEX CCD diffractometer	3022 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2039 reflections with I > 2σ(I)
T_min = 0.498, T_max = 0.614	R_int = 0.046
16108 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.58 e Å⁻³
3022 reflections	Δρ_min = −0.63 e Å⁻³
224 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y−1, z; (ii) −x+1, y+1/2, −z+3/2; (iii) −x+3/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂BrN₃O₄
M_r	390.20
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	14.4725 (11), 6.7744 (5), 31.310 (2)
V (Å³)	3069.8 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.71
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.498, 0.614
No. of measured, independent and observed [I > 2σ(I)] reflections	16108, 3022, 2039
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.096, 1.02
No. of reflections	3022
No. of parameters	224
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.63

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x, y−1, z; (ii) −x+1, y+1/2, −z+3/2; (iii) −x+3/2, y+1/2, z.

Acknowledgements

The work was financed by a project supported by the Hunan Provincial Natural Science Foundation of China (grant No. 11 J J3113), the Key Laboratory of Hunan Forest Products and Chemical Industry Engineering of Hunan Province (grant No. JDZ201102) and by an aid program for the Science and Technology Innovative Research Team (Chemicals of Forestry Resources and Development of Forest Products) in Higher Educational Institutions of Hunan Province.

References

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Volume 67| Part 11| November 2011| Page o3086

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