N'-[(E)-4-Bromo-benzyl-idene]-1-benzofuran-2-carbohydrazide monohydrate.

The title compound, C(16)H(11)BrN(2)O(2)·H(2)O, exists in a trans conformation with respect to the N=C bond [1.2815 (14) Å] and the benzofuran ring system forms a dihedral angle of 2.96 (5)° with the benzene ring. In the crystal, the ketone O atom accepts two O-H⋯O and one C-H⋯O hydrogen bond, and the water O atom accepts an N-H⋯O inter-action. Together, these lead to infinite layers lying parallel to (100).

Related literature

For related structures and background to the biological activity of hydrazones, see: Fun et al. (2012a ▶,b ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H11BrN2O2·H2O

M = 361.19

Monoclinic,

a = 25.0594 (4) Å

b = 4.6718 (1) Å

c = 12.6166 (2) Å

β = 99.175 (1)°

V = 1458.16 (5) Å3

Z = 4

Mo Kα radiation

μ = 2.83 mm−1

T = 100 K

0.41 × 0.22 × 0.13 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.390, T max = 0.708

22903 measured reflections

6458 independent reflections

6000 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.048

S = 1.00

6458 reflections

205 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.55 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 3029 Friedel pairs

Flack parameter: 0.002 (3)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812026724/hb6850sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026724/hb6850Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812026724/hb6850Isup3.cml

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

C16H11BrN2O2·H2O	F(000) = 728
Mr = 361.19	Dx = 1.645 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 9978 reflections
a = 25.0594 (4) Å	θ = 3.3–35.9°
b = 4.6718 (1) Å	µ = 2.83 mm−1
c = 12.6166 (2) Å	T = 100 K
β = 99.175 (1)°	Block, colourless
V = 1458.16 (5) Å3	0.41 × 0.22 × 0.13 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	6458 independent reflections
Radiation source: fine-focus sealed tube	6000 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 35.9°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −38→40
Tmin = 0.390, Tmax = 0.708	k = −7→7
22903 measured reflections	l = −20→20

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.021	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.048	w = 1/[σ2(Fo2) + (0.0159P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
6458 reflections	Δρmax = 0.55 e Å−3
205 parameters	Δρmin = −0.24 e Å−3
2 restraints	Absolute structure: Flack (1983), 3029 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.002 (3)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.493770 (6)	1.100705 (19)	0.508751 (8)	0.02217 (3)
O1	0.18964 (3)	−0.55368 (16)	0.27425 (6)	0.01388 (14)
O2	0.23751 (3)	−0.22894 (17)	0.52806 (6)	0.01613 (14)
N1	0.25775 (4)	−0.12217 (17)	0.36132 (8)	0.01253 (15)
N2	0.29362 (4)	0.08563 (17)	0.40538 (8)	0.01311 (15)
C1	0.15501 (5)	−0.6274 (2)	0.42754 (10)	0.0167 (2)
H1A	0.1499	−0.6159	0.4988	0.020*
C2	0.12501 (5)	−0.7988 (2)	0.34457 (9)	0.01525 (18)
C3	0.08115 (5)	−0.9889 (3)	0.33817 (10)	0.0212 (2)
H3A	0.0646	−1.0253	0.3978	0.025*
C4	0.06318 (5)	−1.1207 (2)	0.24052 (10)	0.0196 (2)
H4A	0.0339	−1.2455	0.2343	0.024*
C5	0.08847 (5)	−1.0683 (2)	0.15094 (11)	0.0174 (2)
H5A	0.0757	−1.1616	0.0868	0.021*
C6	0.13193 (7)	−0.8818 (2)	0.15468 (11)	0.0167 (2)
H6A	0.1489	−0.8486	0.0955	0.020*
C7	0.14821 (4)	−0.7488 (2)	0.25269 (9)	0.01312 (17)
C8	0.19229 (4)	−0.4854 (2)	0.38103 (9)	0.01323 (17)
C9	0.23162 (4)	−0.2696 (2)	0.42951 (9)	0.01253 (17)
C10	0.32052 (4)	0.2111 (2)	0.34060 (9)	0.01383 (17)
H10A	0.3147	0.1628	0.2682	0.017*
C11	0.36048 (6)	0.4314 (2)	0.38081 (11)	0.0136 (2)
C12	0.39181 (5)	0.5549 (2)	0.31113 (11)	0.0176 (2)
H12A	0.3860	0.5028	0.2391	0.021*
C13	0.43169 (5)	0.7550 (2)	0.34769 (10)	0.0184 (2)
H13A	0.4531	0.8332	0.3012	0.022*
C14	0.43889 (5)	0.8351 (2)	0.45464 (10)	0.0167 (2)
C15	0.40692 (5)	0.7233 (2)	0.52486 (9)	0.0175 (2)
H15A	0.4116	0.7844	0.5959	0.021*
C16	0.36790 (5)	0.5192 (2)	0.48830 (9)	0.01555 (19)
H16A	0.3467	0.4410	0.5352	0.019*
O1W	0.27065 (4)	0.74269 (17)	0.14979 (7)	0.01805 (15)
H2W1	0.2695	0.8848	0.1077	0.010 (4)*
H1W1	0.2584	0.5915	0.1236	0.039 (6)*
H1N1	0.2547 (7)	−0.166 (4)	0.2920 (14)	0.020 (4)*

	U11	U22	U33	U12	U13	U23
Br1	0.01396 (4)	0.01463 (4)	0.03562 (7)	−0.00355 (5)	−0.00306 (4)	0.00589 (5)
O1	0.0141 (4)	0.0144 (3)	0.0133 (4)	−0.0033 (2)	0.0027 (3)	−0.0009 (2)
O2	0.0209 (4)	0.0149 (3)	0.0130 (3)	−0.0020 (3)	0.0039 (3)	−0.0014 (2)
N1	0.0136 (4)	0.0121 (3)	0.0119 (4)	−0.0020 (3)	0.0022 (3)	−0.0012 (3)
N2	0.0126 (4)	0.0113 (3)	0.0150 (4)	−0.0019 (3)	0.0009 (3)	−0.0012 (3)
C1	0.0201 (5)	0.0172 (5)	0.0136 (5)	−0.0042 (3)	0.0053 (4)	−0.0019 (3)
C2	0.0153 (5)	0.0148 (4)	0.0160 (5)	−0.0031 (3)	0.0035 (4)	−0.0005 (3)
C3	0.0224 (6)	0.0227 (5)	0.0197 (6)	−0.0093 (4)	0.0069 (4)	−0.0013 (4)
C4	0.0179 (5)	0.0197 (5)	0.0209 (6)	−0.0075 (4)	0.0017 (4)	−0.0007 (4)
C5	0.0183 (5)	0.0177 (4)	0.0152 (5)	−0.0016 (3)	0.0001 (4)	−0.0015 (3)
C6	0.0183 (6)	0.0197 (5)	0.0123 (5)	−0.0014 (4)	0.0028 (4)	0.0003 (4)
C7	0.0119 (4)	0.0116 (4)	0.0159 (5)	−0.0013 (3)	0.0025 (4)	0.0008 (3)
C8	0.0145 (4)	0.0122 (4)	0.0128 (5)	−0.0014 (3)	0.0016 (4)	−0.0019 (3)
C9	0.0127 (4)	0.0111 (4)	0.0139 (5)	0.0001 (3)	0.0022 (4)	−0.0003 (3)
C10	0.0147 (5)	0.0132 (4)	0.0136 (5)	−0.0003 (3)	0.0023 (4)	−0.0001 (3)
C11	0.0130 (5)	0.0121 (4)	0.0157 (5)	0.0017 (3)	0.0023 (4)	0.0023 (3)
C12	0.0190 (5)	0.0172 (4)	0.0176 (5)	−0.0006 (4)	0.0061 (4)	0.0020 (4)
C13	0.0163 (5)	0.0167 (4)	0.0232 (6)	−0.0012 (3)	0.0060 (4)	0.0046 (4)
C14	0.0131 (5)	0.0121 (4)	0.0239 (6)	−0.0006 (3)	0.0004 (4)	0.0041 (3)
C15	0.0170 (5)	0.0168 (4)	0.0178 (5)	−0.0034 (3)	0.0002 (4)	0.0016 (4)
C16	0.0152 (5)	0.0156 (4)	0.0159 (5)	−0.0030 (3)	0.0024 (4)	0.0006 (3)
O1W	0.0251 (4)	0.0160 (3)	0.0129 (4)	−0.0005 (3)	0.0026 (3)	0.0005 (3)

Br1—C14	1.8967 (11)	C5—H5A	0.9300
O1—C7	1.3757 (13)	C6—C7	1.3860 (17)
O1—C8	1.3757 (13)	C6—H6A	0.9300
O2—C9	1.2431 (13)	C8—C9	1.4730 (15)
N1—C9	1.3501 (14)	C10—C11	1.4686 (17)
N1—N2	1.3783 (12)	C10—H10A	0.9300
N1—H1N1	0.890 (17)	C11—C12	1.3938 (18)
N2—C10	1.2815 (14)	C11—C16	1.4006 (18)
C1—C8	1.3537 (16)	C12—C13	1.3923 (17)
C1—C2	1.4323 (16)	C12—H12A	0.9300
C1—H1A	0.9300	C13—C14	1.3841 (18)
C2—C7	1.3970 (15)	C13—H13A	0.9300
C2—C3	1.4054 (16)	C14—C15	1.3879 (16)
C3—C4	1.3865 (18)	C15—C16	1.3906 (16)
C3—H3A	0.9300	C15—H15A	0.9300
C4—C5	1.4027 (19)	C16—H16A	0.9300
C4—H4A	0.9300	O1W—H2W1	0.8477
C5—C6	1.3895 (19)	O1W—H1W1	0.8182
C7—O1—C8	105.33 (8)	C1—C8—C9	128.15 (10)
C9—N1—N2	116.97 (9)	O1—C8—C9	119.35 (9)
C9—N1—H1N1	122.2 (12)	O2—C9—N1	124.56 (10)
N2—N1—H1N1	120.5 (12)	O2—C9—C8	119.00 (10)
C10—N2—N1	116.14 (9)	N1—C9—C8	116.41 (9)
C8—C1—C2	105.98 (10)	N2—C10—C11	119.96 (10)
C8—C1—H1A	127.0	N2—C10—H10A	120.0
C2—C1—H1A	127.0	C11—C10—H10A	120.0
C7—C2—C3	118.90 (10)	C12—C11—C16	119.23 (12)
C7—C2—C1	105.87 (9)	C12—C11—C10	119.59 (12)
C3—C2—C1	135.23 (11)	C16—C11—C10	121.17 (11)
C4—C3—C2	118.16 (11)	C13—C12—C11	121.05 (12)
C4—C3—H3A	120.9	C13—C12—H12A	119.5
C2—C3—H3A	120.9	C11—C12—H12A	119.5
C3—C4—C5	120.93 (11)	C14—C13—C12	118.66 (11)
C3—C4—H4A	119.5	C14—C13—H13A	120.7
C5—C4—H4A	119.5	C12—C13—H13A	120.7
C6—C5—C4	122.31 (12)	C13—C14—C15	121.45 (11)
C6—C5—H5A	118.8	C13—C14—Br1	120.14 (9)
C4—C5—H5A	118.8	C15—C14—Br1	118.41 (9)
C7—C6—C5	115.40 (12)	C14—C15—C16	119.56 (11)
C7—C6—H6A	122.3	C14—C15—H15A	120.2
C5—C6—H6A	122.3	C16—C15—H15A	120.2
O1—C7—C6	125.38 (10)	C15—C16—C11	119.98 (11)
O1—C7—C2	110.34 (9)	C15—C16—H16A	120.0
C6—C7—C2	124.27 (10)	C11—C16—H16A	120.0
C1—C8—O1	112.45 (9)	H2W1—O1W—H1W1	116.8
C9—N1—N2—C10	175.83 (10)	N2—N1—C9—O2	0.50 (15)
C8—C1—C2—C7	1.26 (13)	N2—N1—C9—C8	178.34 (9)
C8—C1—C2—C3	−178.77 (14)	C1—C8—C9—O2	9.58 (17)
C7—C2—C3—C4	0.58 (18)	O1—C8—C9—O2	−173.05 (9)
C1—C2—C3—C4	−179.38 (13)	C1—C8—C9—N1	−168.39 (11)
C2—C3—C4—C5	0.73 (19)	O1—C8—C9—N1	8.97 (14)
C3—C4—C5—C6	−0.7 (2)	N1—N2—C10—C11	−178.76 (9)
C4—C5—C6—C7	−0.66 (19)	N2—C10—C11—C12	176.26 (11)
C8—O1—C7—C6	−178.42 (11)	N2—C10—C11—C16	−3.47 (17)
C8—O1—C7—C2	0.63 (11)	C16—C11—C12—C13	2.60 (18)
C5—C6—C7—O1	−178.99 (10)	C10—C11—C12—C13	−177.13 (11)
C5—C6—C7—C2	2.09 (18)	C11—C12—C13—C14	−1.58 (17)
C3—C2—C7—O1	178.84 (10)	C12—C13—C14—C15	−0.80 (17)
C1—C2—C7—O1	−1.19 (12)	C12—C13—C14—Br1	178.62 (9)
C3—C2—C7—C6	−2.09 (18)	C13—C14—C15—C16	2.11 (17)
C1—C2—C7—C6	177.88 (11)	Br1—C14—C15—C16	−177.32 (9)
C2—C1—C8—O1	−0.94 (13)	C14—C15—C16—C11	−1.05 (17)
C2—C1—C8—C9	176.58 (10)	C12—C11—C16—C15	−1.26 (18)
C7—O1—C8—C1	0.21 (12)	C10—C11—C16—C15	178.47 (11)
C7—O1—C8—C9	−177.55 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W1···O2i	0.85	2.00	2.7932 (11)	157
O1W—H1W1···O2ii	0.82	2.10	2.8987 (11)	167
N1—H1N1···O1Wiii	0.890 (17)	1.947 (18)	2.8108 (13)	163.4 (17)
C6—H6A···O2iv	0.93	2.53	3.3418 (18)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H2W1⋯O2i	0.85	2.00	2.7932 (11)	157
O1W—H1W1⋯O2ii	0.82	2.10	2.8987 (11)	167
N1—H1N1⋯O1W iii	0.890 (17)	1.947 (18)	2.8108 (13)	163.4 (17)
C6—H6A⋯O2iv	0.93	2.53	3.3418 (18)	146

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