N'-[(E)-(3-Phenyl-1H-pyrazol-4-yl)methyl-idene]naphtho-[2,1-b]furan-2-carbohydrazide monohydrate.

In the title hydrate, C(23)H(16)N(4)O(2)·H(2)O, the pyrazole ring is approximately planar, with a maximum deviation of 0.023 (1) Å, and makes dihedral angles of 28.63 (6) and 46.44 (7)° with the naphtho-[2,1-b]furan ring system and the benzene ring, respectively, In the crystal, O-H⋯N, O-H⋯O, N-H⋯O, N-H⋯N, C-H⋯O and C-H⋯N hydrogen bonds link the mol-ecules, forming sheets lying parallel to the ab plane. The crystal structure also features C-H⋯π inter-actions involving the centroids of the pyrazole and benzene rings.

Related literature

For the biological activity of hydrazides, hydrazones and their adducts, see: Jahagirdar et al. (1990 ▶); Cavier & Rips (1965 ▶); Silva et al. (2005 ▶); Eissa & Soliman (2009 ▶). For a related structure, see: Choi et al. (2009 ▶). For the stability of the temperature controller used in the the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C23H16N4O2·H2O

M = 398.41

Monoclinic,

a = 7.1383 (1) Å

b = 9.3928 (1) Å

c = 28.4200 (4) Å

β = 96.864 (1)°

V = 1891.86 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.31 × 0.25 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.971, T max = 0.983

21248 measured reflections

5516 independent reflections

3857 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.129

S = 1.03

5516 reflections

279 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.27 e Å−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/S1600536811050239/hb6529sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050239/hb6529Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811050239/hb6529Isup3.cml

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

C23H16N4O2·H2O	F(000) = 832
Mr = 398.41	Dx = 1.399 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3650 reflections
a = 7.1383 (1) Å	θ = 2.3–29.5°
b = 9.3928 (1) Å	µ = 0.10 mm−1
c = 28.4200 (4) Å	T = 100 K
β = 96.864 (1)°	Block, colourless
V = 1891.86 (4) Å3	0.31 × 0.25 × 0.18 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	5516 independent reflections
Radiation source: fine-focus sealed tube	3857 reflections with I > 2σ(I)
graphite	Rint = 0.058
φ and ω scans	θmax = 30.1°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→10
Tmin = 0.971, Tmax = 0.983	k = −13→13
21248 measured reflections	l = −39→40

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0566P)2 + 0.4389P] where P = (Fo2 + 2Fc2)/3
5516 reflections	(Δ/σ)max < 0.001
279 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.27 e Å−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 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
O1	0.43329 (14)	1.04167 (12)	0.06904 (4)	0.0190 (2)
O2	0.91817 (15)	1.01592 (13)	0.11647 (4)	0.0251 (3)
N1	0.65264 (19)	0.90451 (14)	0.13601 (4)	0.0177 (3)
N2	0.75457 (18)	0.82808 (14)	0.17263 (4)	0.0177 (3)
N3	0.93853 (18)	0.49668 (15)	0.27204 (5)	0.0196 (3)
N4	0.78932 (17)	0.40748 (14)	0.26062 (5)	0.0196 (3)
C1	0.3524 (2)	1.12767 (17)	0.03335 (5)	0.0183 (3)
C2	0.1589 (2)	1.13360 (19)	0.01844 (6)	0.0232 (3)
H2A	0.0711	1.0769	0.0327	0.028*
C3	0.1027 (2)	1.22541 (19)	−0.01779 (6)	0.0245 (4)
H3A	−0.0275	1.2308	−0.0294	0.029*
C4	0.2337 (2)	1.31378 (18)	−0.03878 (6)	0.0212 (3)
C5	0.1705 (2)	1.41189 (19)	−0.07502 (6)	0.0242 (4)
H5A	0.0398	1.4178	−0.0861	0.029*
C6	0.2963 (2)	1.49881 (18)	−0.09438 (6)	0.0248 (4)
H6A	0.2514	1.5661	−0.1180	0.030*
C7	0.4909 (2)	1.48864 (18)	−0.07936 (6)	0.0238 (3)
H7A	0.5772	1.5474	−0.0934	0.029*
C8	0.5563 (2)	1.39364 (17)	−0.04433 (6)	0.0210 (3)
H8A	0.6878	1.3874	−0.0343	0.025*
C9	0.4303 (2)	1.30561 (17)	−0.02320 (5)	0.0185 (3)
C10	0.4875 (2)	1.20827 (16)	0.01465 (5)	0.0170 (3)
C11	0.6639 (2)	1.17157 (17)	0.04153 (5)	0.0188 (3)
H11A	0.7846	1.2095	0.0377	0.023*
C12	0.6241 (2)	1.07205 (17)	0.07342 (5)	0.0175 (3)
C13	0.7456 (2)	0.99555 (17)	0.11028 (5)	0.0184 (3)
C14	0.6704 (2)	0.71368 (16)	0.18341 (5)	0.0167 (3)
H14A	0.5497	0.6931	0.1669	0.020*
C15	0.7500 (2)	0.61507 (16)	0.21930 (5)	0.0166 (3)
C16	0.9210 (2)	0.61994 (17)	0.24849 (5)	0.0185 (3)
H16A	1.0087	0.6965	0.2512	0.022*
C17	0.6738 (2)	0.47933 (16)	0.22852 (5)	0.0168 (3)
C18	0.4979 (2)	0.41425 (16)	0.20556 (5)	0.0169 (3)
C19	0.4996 (2)	0.27495 (17)	0.18791 (5)	0.0197 (3)
H19A	0.6122	0.2203	0.1927	0.024*
C20	0.3376 (2)	0.21643 (18)	0.16353 (6)	0.0229 (3)
H20A	0.3396	0.1219	0.1517	0.027*
C21	0.1728 (2)	0.29580 (19)	0.15644 (6)	0.0236 (4)
H21A	0.0629	0.2564	0.1391	0.028*
C22	0.1685 (2)	0.43245 (18)	0.17454 (5)	0.0209 (3)
H22A	0.0550	0.4862	0.1700	0.025*
C23	0.3301 (2)	0.49127 (17)	0.19929 (5)	0.0187 (3)
H23A	0.3259	0.5846	0.2120	0.022*
O1W	0.25339 (16)	0.83476 (13)	0.13979 (4)	0.0270 (3)
H1W1	0.2518	0.8380	0.1701	0.041*
H2W1	0.1460	0.8694	0.1251	0.041*
H1N3	1.036 (3)	0.467 (3)	0.2959 (9)	0.064 (8)*
H1N1	0.523 (4)	0.888 (3)	0.1276 (9)	0.061 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0172 (5)	0.0208 (6)	0.0183 (5)	−0.0003 (4)	−0.0002 (4)	0.0029 (4)
O2	0.0196 (6)	0.0262 (6)	0.0277 (6)	−0.0049 (5)	−0.0040 (4)	0.0068 (5)
N1	0.0180 (6)	0.0176 (6)	0.0168 (6)	−0.0007 (5)	−0.0016 (5)	0.0038 (5)
N2	0.0193 (6)	0.0173 (6)	0.0158 (6)	0.0009 (5)	−0.0011 (5)	0.0011 (5)
N3	0.0163 (6)	0.0231 (7)	0.0185 (6)	−0.0006 (5)	−0.0014 (5)	0.0028 (6)
N4	0.0175 (6)	0.0204 (7)	0.0203 (7)	0.0000 (5)	0.0005 (5)	0.0027 (5)
C1	0.0208 (7)	0.0189 (7)	0.0150 (7)	0.0015 (6)	0.0013 (6)	0.0009 (6)
C2	0.0181 (8)	0.0287 (9)	0.0229 (8)	−0.0027 (7)	0.0024 (6)	0.0043 (7)
C3	0.0189 (8)	0.0305 (9)	0.0238 (8)	0.0017 (7)	0.0017 (6)	0.0034 (7)
C4	0.0222 (8)	0.0233 (8)	0.0178 (7)	0.0020 (7)	0.0017 (6)	0.0003 (6)
C5	0.0240 (8)	0.0289 (9)	0.0191 (8)	0.0053 (7)	0.0004 (6)	0.0024 (7)
C6	0.0334 (9)	0.0234 (8)	0.0176 (8)	0.0068 (7)	0.0025 (6)	0.0032 (7)
C7	0.0299 (9)	0.0229 (8)	0.0192 (8)	−0.0009 (7)	0.0055 (6)	0.0010 (7)
C8	0.0238 (8)	0.0203 (8)	0.0193 (8)	0.0000 (6)	0.0047 (6)	0.0010 (6)
C9	0.0207 (8)	0.0195 (8)	0.0151 (7)	0.0011 (6)	0.0024 (6)	−0.0006 (6)
C10	0.0175 (7)	0.0181 (7)	0.0152 (7)	0.0011 (6)	0.0013 (5)	−0.0003 (6)
C11	0.0173 (7)	0.0194 (8)	0.0195 (7)	0.0003 (6)	0.0011 (6)	0.0002 (6)
C12	0.0161 (7)	0.0181 (7)	0.0179 (7)	−0.0015 (6)	0.0002 (5)	−0.0006 (6)
C13	0.0195 (7)	0.0176 (7)	0.0176 (7)	−0.0015 (6)	−0.0004 (6)	0.0001 (6)
C14	0.0166 (7)	0.0170 (7)	0.0164 (7)	0.0011 (6)	0.0009 (5)	−0.0014 (6)
C15	0.0177 (7)	0.0169 (7)	0.0153 (7)	0.0015 (6)	0.0022 (5)	−0.0008 (6)
C16	0.0180 (7)	0.0202 (8)	0.0173 (7)	−0.0004 (6)	0.0028 (6)	0.0008 (6)
C17	0.0182 (7)	0.0173 (7)	0.0150 (7)	0.0024 (6)	0.0029 (5)	−0.0001 (6)
C18	0.0193 (7)	0.0173 (7)	0.0141 (7)	−0.0024 (6)	0.0020 (5)	0.0027 (6)
C19	0.0223 (8)	0.0179 (8)	0.0194 (8)	0.0008 (6)	0.0039 (6)	0.0021 (6)
C20	0.0292 (9)	0.0193 (8)	0.0213 (8)	−0.0066 (7)	0.0075 (6)	−0.0027 (6)
C21	0.0230 (8)	0.0291 (9)	0.0190 (8)	−0.0091 (7)	0.0035 (6)	−0.0016 (7)
C22	0.0162 (7)	0.0268 (9)	0.0195 (8)	−0.0004 (6)	0.0015 (6)	0.0003 (7)
C23	0.0191 (7)	0.0185 (8)	0.0186 (7)	0.0004 (6)	0.0021 (6)	−0.0007 (6)
O1W	0.0273 (6)	0.0292 (7)	0.0257 (6)	0.0054 (5)	0.0076 (5)	0.0018 (5)

O1—C1	1.3692 (18)	C8—H8A	0.9500
O1—C12	1.3826 (17)	C9—C10	1.433 (2)
O2—C13	1.2383 (18)	C10—C11	1.435 (2)
N1—C13	1.3499 (19)	C11—C12	1.356 (2)
N1—N2	1.3954 (17)	C11—H11A	0.9500
N1—H1N1	0.94 (2)	C12—C13	1.466 (2)
N2—C14	1.2860 (19)	C14—C15	1.443 (2)
N3—C16	1.336 (2)	C14—H14A	0.9500
N3—N4	1.3636 (18)	C15—C16	1.392 (2)
N3—H1N3	0.96 (2)	C15—C17	1.423 (2)
N4—C17	1.3372 (19)	C16—H16A	0.9500
C1—C10	1.381 (2)	C17—C18	1.476 (2)
C1—C2	1.397 (2)	C18—C23	1.393 (2)
C2—C3	1.366 (2)	C18—C19	1.402 (2)
C2—H2A	0.9500	C19—C20	1.389 (2)
C3—C4	1.433 (2)	C19—H19A	0.9500
C3—H3A	0.9500	C20—C21	1.387 (2)
C4—C5	1.415 (2)	C20—H20A	0.9500
C4—C9	1.422 (2)	C21—C22	1.384 (2)
C5—C6	1.376 (2)	C21—H21A	0.9500
C5—H5A	0.9500	C22—C23	1.392 (2)
C6—C7	1.407 (2)	C22—H22A	0.9500
C6—H6A	0.9500	C23—H23A	0.9500
C7—C8	1.376 (2)	O1W—H1W1	0.8628
C7—H7A	0.9500	O1W—H2W1	0.8895
C8—C9	1.408 (2)
C1—O1—C12	105.57 (12)	C12—C11—H11A	126.8
C13—N1—N2	118.93 (13)	C10—C11—H11A	126.8
C13—N1—H1N1	119.8 (15)	C11—C12—O1	111.43 (13)
N2—N1—H1N1	121.1 (15)	C11—C12—C13	131.48 (14)
C14—N2—N1	113.00 (12)	O1—C12—C13	117.09 (13)
C16—N3—N4	112.94 (13)	O2—C13—N1	124.46 (14)
C16—N3—H1N3	128.8 (15)	O2—C13—C12	121.30 (14)
N4—N3—H1N3	118.2 (15)	N1—C13—C12	114.24 (13)
C17—N4—N3	104.65 (13)	N2—C14—C15	123.27 (14)
O1—C1—C10	110.89 (13)	N2—C14—H14A	118.4
O1—C1—C2	124.22 (14)	C15—C14—H14A	118.4
C10—C1—C2	124.89 (14)	C16—C15—C17	104.31 (13)
C3—C2—C1	116.37 (15)	C16—C15—C14	130.05 (14)
C3—C2—H2A	121.8	C17—C15—C14	125.31 (14)
C1—C2—H2A	121.8	N3—C16—C15	107.04 (14)
C2—C3—C4	122.18 (15)	N3—C16—H16A	126.5
C2—C3—H3A	118.9	C15—C16—H16A	126.5
C4—C3—H3A	118.9	N4—C17—C15	111.07 (13)
C5—C4—C9	118.60 (15)	N4—C17—C18	121.01 (14)
C5—C4—C3	120.88 (15)	C15—C17—C18	127.84 (13)
C9—C4—C3	120.51 (14)	C23—C18—C19	118.89 (14)
C6—C5—C4	120.73 (15)	C23—C18—C17	120.96 (14)
C6—C5—H5A	119.6	C19—C18—C17	120.10 (14)
C4—C5—H5A	119.6	C20—C19—C18	120.38 (15)
C5—C6—C7	120.41 (15)	C20—C19—H19A	119.8
C5—C6—H6A	119.8	C18—C19—H19A	119.8
C7—C6—H6A	119.8	C21—C20—C19	120.06 (15)
C8—C7—C6	120.04 (15)	C21—C20—H20A	120.0
C8—C7—H7A	120.0	C19—C20—H20A	120.0
C6—C7—H7A	120.0	C22—C21—C20	120.04 (15)
C7—C8—C9	120.71 (15)	C22—C21—H21A	120.0
C7—C8—H8A	119.6	C20—C21—H21A	120.0
C9—C8—H8A	119.6	C21—C22—C23	120.13 (15)
C8—C9—C4	119.48 (14)	C21—C22—H22A	119.9
C8—C9—C10	123.75 (14)	C23—C22—H22A	119.9
C4—C9—C10	116.75 (14)	C22—C23—C18	120.45 (15)
C1—C10—C9	119.27 (14)	C22—C23—H23A	119.8
C1—C10—C11	105.79 (13)	C18—C23—H23A	119.8
C9—C10—C11	134.91 (14)	H1W1—O1W—H2W1	110.0
C12—C11—C10	106.30 (13)
C13—N1—N2—C14	−157.33 (14)	C1—O1—C12—C11	−0.81 (17)
C16—N3—N4—C17	−0.15 (17)	C1—O1—C12—C13	178.90 (13)
C12—O1—C1—C10	1.37 (17)	N2—N1—C13—O2	0.8 (2)
C12—O1—C1—C2	−177.96 (15)	N2—N1—C13—C12	−178.86 (13)
O1—C1—C2—C3	−179.88 (15)	C11—C12—C13—O2	−0.6 (3)
C10—C1—C2—C3	0.9 (3)	O1—C12—C13—O2	179.70 (14)
C1—C2—C3—C4	−1.5 (3)	C11—C12—C13—N1	178.97 (16)
C2—C3—C4—C5	−177.51 (16)	O1—C12—C13—N1	−0.7 (2)
C2—C3—C4—C9	1.8 (3)	N1—N2—C14—C15	178.31 (13)
C9—C4—C5—C6	−0.8 (2)	N2—C14—C15—C16	0.5 (3)
C3—C4—C5—C6	178.56 (16)	N2—C14—C15—C17	−171.90 (14)
C4—C5—C6—C7	1.8 (3)	N4—N3—C16—C15	0.06 (17)
C5—C6—C7—C8	−1.5 (3)	C17—C15—C16—N3	0.06 (16)
C6—C7—C8—C9	0.1 (2)	C14—C15—C16—N3	−173.53 (15)
C7—C8—C9—C4	0.9 (2)	N3—N4—C17—C15	0.18 (16)
C7—C8—C9—C10	−177.53 (15)	N3—N4—C17—C18	177.03 (13)
C5—C4—C9—C8	−0.6 (2)	C16—C15—C17—N4	−0.15 (17)
C3—C4—C9—C8	−179.93 (15)	C14—C15—C17—N4	173.83 (14)
C5—C4—C9—C10	177.97 (14)	C16—C15—C17—C18	−176.73 (14)
C3—C4—C9—C10	−1.4 (2)	C14—C15—C17—C18	−2.8 (2)
O1—C1—C10—C9	−179.87 (13)	N4—C17—C18—C23	136.78 (15)
C2—C1—C10—C9	−0.5 (2)	C15—C17—C18—C23	−46.9 (2)
O1—C1—C10—C11	−1.39 (17)	N4—C17—C18—C19	−45.9 (2)
C2—C1—C10—C11	177.93 (15)	C15—C17—C18—C19	130.41 (16)
C8—C9—C10—C1	179.24 (15)	C23—C18—C19—C20	1.6 (2)
C4—C9—C10—C1	0.8 (2)	C17—C18—C19—C20	−175.76 (14)
C8—C9—C10—C11	1.3 (3)	C18—C19—C20—C21	0.1 (2)
C4—C9—C10—C11	−177.16 (16)	C19—C20—C21—C22	−1.4 (2)
C1—C10—C11—C12	0.84 (17)	C20—C21—C22—C23	0.9 (2)
C9—C10—C11—C12	178.97 (17)	C21—C22—C23—C18	0.8 (2)
C10—C11—C12—O1	−0.02 (18)	C19—C18—C23—C22	−2.1 (2)
C10—C11—C12—C13	−179.69 (16)	C17—C18—C23—C22	175.28 (14)

Cg1 and Cg2 are the centroids of the C18–C23 and N3/N4/C17/C15/C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···N4i	0.86	2.13	2.9625 (18)	163
O1W—H2W1···O2ii	0.89	2.12	2.9465 (16)	154
N3—H1N3···O2iii	0.95 (2)	2.52 (3)	3.2162 (18)	130.4 (19)
N3—H1N3···N2iii	0.95 (2)	2.10 (3)	2.9927 (19)	155 (2)
N1—H1N1···O1W	0.94 (3)	2.06 (3)	2.9388 (18)	155 (2)
C14—H14A···O1W	0.95	2.54	3.2877 (18)	136
C16—H16A···N4iv	0.95	2.50	3.430 (2)	167
C21—H21A···O2v	0.95	2.53	3.318 (2)	140
C7—H7A···Cg2vi	0.95	2.80	3.6022 (18)	142
C22—H22A···Cg1ii	0.95	2.93	3.5274 (16)	122

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C18–C23 and N3/N4/C15–C17 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯N4i	0.86	2.13	2.9625 (18)	163
O1W—H2W1⋯O2ii	0.89	2.12	2.9465 (16)	154
N3—H1N3⋯O2iii	0.95 (2)	2.52 (3)	3.2162 (18)	130.4 (19)
N3—H1N3⋯N2iii	0.95 (2)	2.10 (3)	2.9927 (19)	155 (2)
N1—H1N1⋯O1W	0.94 (3)	2.06 (3)	2.9388 (18)	155 (2)
C14—H14A⋯O1W	0.95	2.54	3.2877 (18)	136
C16—H16A⋯N4iv	0.95	2.50	3.430 (2)	167
C21—H21A⋯O2v	0.95	2.53	3.318 (2)	140
C7—H7A⋯Cg2vi	0.95	2.80	3.6022 (18)	142
C22—H22A⋯Cg1ii	0.95	2.93	3.5274 (16)	122

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