N'-[(E)-3-Bromo-5-chloro-2-hy-droxy-benzyl-idene]furan-2-carbohydrazide.

In the title compound, C12H8BrClN2O3, the furan ring makes a dihedral angle of 17.2 (2)° with the six-membered ring. An intra-molecular O-H⋯N hydrogen bond stabilizes the mol-ecular conformation. In the crystal, N-H⋯O hydrogen bonds connect the mol-ecules into chains running along the c-axis direction. The crystal packing is additionally stabilized by C-H⋯O inter-actions into a three-dimensional supramolecular architecture.

Related literature

Heterocyclic carbohydrazides form stable metal chelates which find applications in mol­ecular sensing, see: Bakir & Brown (2002 ▶). For the biological activity of hydrazones derived from isoniazid (systematic name: isonicotinohydrazide), see: Rollas & Kucukguzel (2007 ▶). For related structures, see: Prabhu et al. (2011 ▶); Bikas et al. (2010 ▶); Prasanna et al. (2013 ▶).

Experimental

Crystal data

C12H8BrClN2O3

M = 343.56

Monoclinic,

a = 16.7237 (9) Å

b = 7.7455 (4) Å

c = 10.1868 (5) Å

β = 93.557 (2)°

V = 1316.99 (12) Å3

Z = 4

Mo Kα radiation

μ = 3.33 mm−1

T = 293 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker AAPEXII CCD Diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.324, T max = 0.435

13728 measured reflections

2996 independent reflections

2029 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.085

S = 1.02

2996 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681401085X/bt6980sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681401085X/bt6980Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681401085X/bt6980Isup3.cml

CCDC reference: 1002445

Additional supporting information: crystallographic information; 3D view; checkCIF report

C12H8BrClN2O3	F(000) = 680
Mr = 343.56	Dx = 1.733 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4049 reflections
a = 16.7237 (9) Å	θ = 2.8–24.5°
b = 7.7455 (4) Å	µ = 3.33 mm−1
c = 10.1868 (5) Å	T = 293 K
β = 93.557 (2)°	Block, yellow
V = 1316.99 (12) Å3	0.35 × 0.30 × 0.25 mm
Z = 4

Bruker AAPEXII CCD Diffractometer	2996 independent reflections
Radiation source: fine-focus sealed tube	2029 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω and φ scan	θmax = 27.4°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −21→21
Tmin = 0.324, Tmax = 0.435	k = −10→8
13728 measured reflections	l = −13→13

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0346P)2 + 0.5776P] where P = (Fo2 + 2Fc2)/3
2996 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.34 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
C1	0.30900 (18)	0.0948 (4)	0.5312 (4)	0.0704 (9)
H1	0.2756	0.0562	0.5947	0.084*
C2	0.28824 (18)	0.1059 (4)	0.4065 (3)	0.0678 (8)
H2	0.2389	0.0761	0.3657	0.081*
C3	0.35486 (17)	0.1718 (4)	0.3450 (2)	0.0558 (7)
H3	0.3579	0.1954	0.2560	0.067*
C4	0.41272 (14)	0.1937 (3)	0.4394 (2)	0.0386 (5)
C5	0.49358 (14)	0.2608 (3)	0.4308 (2)	0.0388 (5)
C6	0.66294 (15)	0.3109 (3)	0.6435 (2)	0.0410 (6)
H6	0.6461	0.2574	0.7187	0.049*
C7	0.74492 (14)	0.3741 (3)	0.6395 (2)	0.0377 (5)
C8	0.76987 (14)	0.4658 (3)	0.5306 (2)	0.0383 (5)
C9	0.84795 (15)	0.5274 (3)	0.5343 (2)	0.0467 (6)
C10	0.90118 (15)	0.4977 (3)	0.6409 (3)	0.0516 (7)
H10	0.9531	0.5410	0.6421	0.062*
C11	0.87656 (16)	0.4041 (3)	0.7446 (2)	0.0484 (6)
C12	0.79961 (15)	0.3424 (3)	0.7459 (2)	0.0458 (6)
H12	0.7839	0.2796	0.8178	0.055*
N1	0.53833 (11)	0.2682 (3)	0.54589 (17)	0.0418 (5)
H1A	0.5194	0.2354	0.6184	0.050*
N2	0.61464 (12)	0.3296 (2)	0.54270 (18)	0.0410 (5)
O1	0.38640 (12)	0.1475 (3)	0.55681 (17)	0.0626 (5)
O2	0.51905 (11)	0.3068 (3)	0.32640 (15)	0.0575 (5)
O3	0.72099 (10)	0.4955 (2)	0.42286 (14)	0.0485 (4)
H3A	0.6769	0.4528	0.4330	0.073*
Cl1	0.94376 (5)	0.36440 (11)	0.87885 (8)	0.0748 (2)
Br1	0.881917 (19)	0.65331 (5)	0.38959 (3)	0.07798 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0489 (18)	0.075 (2)	0.090 (2)	−0.0171 (16)	0.0222 (16)	0.0091 (18)
C2	0.0467 (18)	0.069 (2)	0.086 (2)	−0.0055 (15)	−0.0126 (16)	−0.0198 (17)
C3	0.0533 (17)	0.081 (2)	0.0322 (12)	0.0000 (15)	−0.0055 (11)	−0.0015 (12)
C4	0.0414 (14)	0.0433 (14)	0.0314 (11)	−0.0011 (11)	0.0038 (10)	−0.0031 (10)
C5	0.0415 (14)	0.0453 (14)	0.0299 (11)	0.0020 (11)	0.0034 (10)	−0.0031 (10)
C6	0.0397 (14)	0.0484 (15)	0.0350 (12)	0.0023 (11)	0.0024 (10)	0.0026 (10)
C7	0.0378 (13)	0.0383 (13)	0.0367 (12)	0.0038 (10)	−0.0010 (9)	−0.0033 (10)
C8	0.0379 (13)	0.0399 (14)	0.0369 (11)	0.0030 (11)	−0.0006 (10)	−0.0007 (10)
C9	0.0444 (15)	0.0466 (15)	0.0493 (13)	0.0000 (12)	0.0038 (11)	0.0031 (11)
C10	0.0383 (15)	0.0494 (16)	0.0663 (17)	−0.0004 (12)	−0.0044 (12)	−0.0011 (13)
C11	0.0464 (15)	0.0478 (15)	0.0487 (14)	0.0079 (12)	−0.0145 (11)	−0.0041 (12)
C12	0.0480 (15)	0.0473 (15)	0.0411 (13)	0.0043 (12)	−0.0045 (11)	0.0035 (11)
N1	0.0348 (11)	0.0605 (13)	0.0302 (9)	−0.0051 (10)	0.0035 (8)	0.0000 (9)
N2	0.0353 (11)	0.0491 (12)	0.0385 (10)	−0.0011 (9)	0.0028 (8)	−0.0032 (9)
O1	0.0529 (12)	0.0929 (15)	0.0428 (10)	−0.0065 (11)	0.0091 (8)	0.0075 (9)
O2	0.0502 (11)	0.0906 (14)	0.0323 (9)	−0.0104 (10)	0.0073 (8)	0.0032 (9)
O3	0.0406 (10)	0.0673 (12)	0.0368 (8)	−0.0025 (8)	−0.0027 (7)	0.0072 (8)
Cl1	0.0626 (5)	0.0837 (6)	0.0734 (5)	0.0051 (4)	−0.0337 (4)	0.0057 (4)
Br1	0.0531 (2)	0.1004 (3)	0.0810 (2)	−0.01171 (17)	0.00947 (15)	0.03418 (18)

C1—C2	1.299 (4)	C7—C12	1.396 (3)
C1—O1	1.367 (4)	C7—C8	1.403 (3)
C1—H1	0.9300	C8—O3	1.347 (3)
C2—C3	1.407 (4)	C8—C9	1.388 (3)
C2—H2	0.9300	C9—C10	1.380 (3)
C3—C4	1.332 (3)	C9—Br1	1.885 (2)
C3—H3	0.9300	C10—C11	1.366 (4)
C4—O1	1.348 (3)	C10—H10	0.9300
C4—C5	1.456 (3)	C11—C12	1.373 (4)
C5—O2	1.224 (3)	C11—Cl1	1.743 (2)
C5—N1	1.352 (3)	C12—H12	0.9300
C6—N2	1.275 (3)	N1—N2	1.364 (3)
C6—C7	1.459 (3)	N1—H1A	0.8600
C6—H6	0.9300	O3—H3A	0.8200
C2—C1—O1	111.1 (3)	O3—C8—C9	119.1 (2)
C2—C1—H1	124.5	O3—C8—C7	122.4 (2)
O1—C1—H1	124.5	C9—C8—C7	118.5 (2)
C1—C2—C3	106.7 (3)	C10—C9—C8	121.6 (2)
C1—C2—H2	126.6	C10—C9—Br1	119.4 (2)
C3—C2—H2	126.6	C8—C9—Br1	119.00 (18)
C4—C3—C2	106.6 (2)	C11—C10—C9	119.1 (2)
C4—C3—H3	126.7	C11—C10—H10	120.5
C2—C3—H3	126.7	C9—C10—H10	120.5
C3—C4—O1	110.1 (2)	C10—C11—C12	121.3 (2)
C3—C4—C5	129.7 (2)	C10—C11—Cl1	119.3 (2)
O1—C4—C5	120.2 (2)	C12—C11—Cl1	119.3 (2)
O2—C5—N1	122.5 (2)	C11—C12—C7	120.0 (2)
O2—C5—C4	122.0 (2)	C11—C12—H12	120.0
N1—C5—C4	115.4 (2)	C7—C12—H12	120.0
N2—C6—C7	119.3 (2)	C5—N1—N2	117.55 (19)
N2—C6—H6	120.4	C5—N1—H1A	121.2
C7—C6—H6	120.4	N2—N1—H1A	121.2
C12—C7—C8	119.4 (2)	C6—N2—N1	119.2 (2)
C12—C7—C6	119.4 (2)	C4—O1—C1	105.5 (2)
C8—C7—C6	121.2 (2)	C8—O3—H3A	109.5
O1—C1—C2—C3	−0.8 (4)	C7—C8—C9—Br1	−179.23 (17)
C1—C2—C3—C4	0.9 (4)	C8—C9—C10—C11	0.7 (4)
C2—C3—C4—O1	−0.7 (3)	Br1—C9—C10—C11	−179.00 (19)
C2—C3—C4—C5	−178.9 (3)	C9—C10—C11—C12	−1.5 (4)
C3—C4—C5—O2	−0.6 (4)	C9—C10—C11—Cl1	179.38 (19)
O1—C4—C5—O2	−178.7 (2)	C10—C11—C12—C7	0.4 (4)
C3—C4—C5—N1	179.5 (3)	Cl1—C11—C12—C7	179.61 (18)
O1—C4—C5—N1	1.4 (3)	C8—C7—C12—C11	1.4 (4)
N2—C6—C7—C12	−175.3 (2)	C6—C7—C12—C11	−178.7 (2)
N2—C6—C7—C8	4.6 (3)	O2—C5—N1—N2	−0.1 (4)
C12—C7—C8—O3	177.6 (2)	C4—C5—N1—N2	179.77 (19)
C6—C7—C8—O3	−2.3 (3)	C7—C6—N2—N1	179.1 (2)
C12—C7—C8—C9	−2.1 (3)	C5—N1—N2—C6	−167.9 (2)
C6—C7—C8—C9	178.0 (2)	C3—C4—O1—C1	0.2 (3)
O3—C8—C9—C10	−178.6 (2)	C5—C4—O1—C1	178.6 (2)
C7—C8—C9—C10	1.1 (4)	C2—C1—O1—C4	0.4 (4)
O3—C8—C9—Br1	1.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.86	2.14	2.953 (2)	157
C3—H3···O1ii	0.93	2.44	3.324 (3)	159
C6—H6···O2i	0.93	2.50	3.263 (3)	139
O3—H3A···N2	0.82	1.84	2.564 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.86	2.14	2.953 (2)	157
C3—H3⋯O1ii	0.93	2.44	3.324 (3)	159
C6—H6⋯O2i	0.93	2.50	3.263 (3)	139
O3—H3A⋯N2	0.82	1.84	2.564 (3)	146

Symmetry codes: (i) ; (ii) .