N'-(3-Fluoro-benzyl-idene)-4-hy-droxy-3-meth-oxy-benzohydrazide methanol monosolvate.

In the title compound, C(15)H(13)FN(2)O(3)·CH(3)OH, the dihedral angle between the benzene rings of the benzohydrazone mol-ecule is 5.3 (3)°. The C atom of the meth-oxy group is almost coplanar with its attached ring [deviation = 0.017 (2) Å]. The r.m.s. deviation of the 21 non-H atoms of the hydrazone mol-ecule is 0.106 Å. In the crystal, the components are linked by O(m)-H⋯O(h), N(h)-H⋯O(m) and O(h)-H⋯O(h) (m = methanol and h = hydrazone) hydrogen bonds, forming (001) layers.

Related literature

For related structures, see: Horkaew et al. (2012) ▶; Fun et al. (2011 ▶); Zhang (2011 ▶).

Experimental

Crystal data

C15H13FN2O3·CH4O

M = 320.32

Orthorhombic,

a = 14.9566 (18) Å

b = 11.1123 (16) Å

c = 19.351 (2) Å

V = 3216.1 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.20 × 0.18 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.980, T max = 0.983

22845 measured reflections

3270 independent reflections

2588 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.161

S = 1.12

3270 reflections

215 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812012196/hb6695sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012196/hb6695Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812012196/hb6695Isup3.cml

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

C15H13FN2O3·CH4O	Dx = 1.323 Mg m−3
Mr = 320.32	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 8503 reflections
a = 14.9566 (18) Å	θ = 2.5–26.0°
b = 11.1123 (16) Å	µ = 0.10 mm−1
c = 19.351 (2) Å	T = 298 K
V = 3216.1 (7) Å3	Block, colorless
Z = 8	0.20 × 0.18 × 0.17 mm
F(000) = 1344

Bruker APEXII CCD diffractometer	3270 independent reflections
Radiation source: fine-focus sealed tube	2588 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 26.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −18→17
Tmin = 0.980, Tmax = 0.983	k = −13→13
22845 measured reflections	l = −24→24

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ2(Fo2) + (0.0956P)2 + 0.5869P] where P = (Fo2 + 2Fc2)/3
3270 reflections	(Δ/σ)max < 0.001
215 parameters	Δρmax = 0.28 e Å−3
1 restraint	Δρmin = −0.34 e Å−3

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
F1	0.62214 (8)	1.20264 (15)	0.71230 (10)	0.0899 (5)
N1	0.27077 (9)	0.93828 (13)	0.59540 (8)	0.0396 (4)
N2	0.33902 (9)	1.00033 (12)	0.62766 (8)	0.0390 (3)
O1	0.02644 (7)	0.56459 (11)	0.42821 (6)	0.0430 (3)
H1A	−0.0236	0.5933	0.4332	0.064*
O2	0.19271 (8)	0.52220 (13)	0.40048 (7)	0.0540 (4)
O3	0.37143 (7)	0.80593 (11)	0.55390 (8)	0.0497 (4)
O4	0.39737 (10)	0.57101 (14)	0.59772 (13)	0.0833 (6)
H4	0.3917	0.6416	0.5862	0.125*
C1	0.38310 (11)	1.16625 (15)	0.69775 (9)	0.0397 (4)
C2	0.35539 (13)	1.26065 (17)	0.73975 (10)	0.0500 (5)
H2	0.2946	1.2747	0.7460	0.060*
C3	0.41710 (15)	1.33379 (19)	0.77229 (11)	0.0585 (5)
H3	0.3976	1.3964	0.8004	0.070*
C4	0.50739 (14)	1.31446 (19)	0.76342 (12)	0.0601 (6)
H4A	0.5494	1.3629	0.7854	0.072*
C5	0.53336 (13)	1.22155 (18)	0.72118 (11)	0.0533 (5)
C6	0.47444 (12)	1.14675 (16)	0.68772 (10)	0.0449 (4)
H6	0.4947	1.0851	0.6593	0.054*
C7	0.31604 (11)	1.09122 (16)	0.66320 (9)	0.0419 (4)
H7	0.2558	1.1105	0.6674	0.050*
C8	0.29236 (10)	0.84020 (15)	0.55851 (9)	0.0361 (4)
C9	0.21891 (10)	0.77204 (14)	0.52525 (9)	0.0351 (4)
C10	0.24240 (10)	0.68253 (15)	0.47763 (9)	0.0383 (4)
H10	0.3023	0.6698	0.4670	0.046*
C11	0.17751 (10)	0.61309 (15)	0.44635 (9)	0.0371 (4)
C12	0.08669 (10)	0.63371 (14)	0.46134 (8)	0.0341 (4)
C13	0.06435 (10)	0.72117 (16)	0.50909 (9)	0.0381 (4)
H13	0.0046	0.7337	0.5201	0.046*
C14	0.12929 (10)	0.79028 (15)	0.54072 (9)	0.0379 (4)
H14	0.1129	0.8492	0.5724	0.046*
C15	0.28296 (14)	0.4987 (2)	0.38116 (13)	0.0658 (6)
H15A	0.3077	0.5685	0.3591	0.099*
H15B	0.2847	0.4318	0.3498	0.099*
H15C	0.3173	0.4798	0.4216	0.099*
C16	0.48620 (15)	0.5484 (2)	0.61393 (16)	0.0715 (7)
H16A	0.5145	0.6218	0.6283	0.107*
H16B	0.5164	0.5171	0.5740	0.107*
H16C	0.4892	0.4906	0.6507	0.107*
H1	0.2134 (9)	0.965 (2)	0.5972 (14)	0.080*

	U11	U22	U33	U12	U13	U23
F1	0.0391 (7)	0.0999 (11)	0.1307 (13)	−0.0092 (7)	−0.0109 (7)	−0.0398 (10)
N1	0.0252 (6)	0.0355 (8)	0.0580 (9)	−0.0004 (5)	−0.0071 (6)	−0.0071 (6)
N2	0.0296 (7)	0.0345 (7)	0.0529 (8)	−0.0032 (5)	−0.0072 (6)	−0.0026 (6)
O1	0.0290 (6)	0.0475 (7)	0.0524 (7)	−0.0020 (5)	−0.0040 (5)	−0.0134 (6)
O2	0.0345 (7)	0.0598 (9)	0.0676 (8)	0.0074 (6)	−0.0031 (6)	−0.0287 (7)
O3	0.0231 (6)	0.0446 (7)	0.0815 (9)	0.0013 (5)	−0.0042 (5)	−0.0166 (6)
O4	0.0364 (8)	0.0443 (9)	0.169 (2)	−0.0031 (6)	−0.0031 (9)	0.0085 (10)
C1	0.0402 (9)	0.0368 (9)	0.0422 (9)	−0.0020 (7)	−0.0044 (7)	−0.0019 (7)
C2	0.0479 (10)	0.0492 (10)	0.0528 (11)	−0.0004 (8)	0.0039 (8)	−0.0106 (9)
C3	0.0659 (13)	0.0514 (12)	0.0583 (12)	−0.0030 (10)	−0.0009 (10)	−0.0193 (9)
C4	0.0610 (13)	0.0533 (12)	0.0659 (13)	−0.0158 (10)	−0.0114 (10)	−0.0157 (10)
C5	0.0407 (10)	0.0546 (12)	0.0646 (12)	−0.0063 (8)	−0.0064 (9)	−0.0086 (10)
C6	0.0410 (9)	0.0414 (9)	0.0524 (10)	−0.0009 (7)	−0.0061 (8)	−0.0082 (8)
C7	0.0318 (8)	0.0421 (9)	0.0519 (10)	0.0004 (7)	−0.0022 (7)	−0.0057 (8)
C8	0.0257 (7)	0.0332 (8)	0.0494 (9)	0.0012 (6)	−0.0016 (6)	0.0000 (7)
C9	0.0266 (7)	0.0331 (8)	0.0456 (9)	−0.0006 (6)	−0.0026 (6)	−0.0007 (7)
C10	0.0241 (7)	0.0397 (9)	0.0511 (9)	0.0034 (6)	−0.0009 (7)	−0.0044 (7)
C11	0.0301 (8)	0.0390 (9)	0.0421 (9)	0.0038 (6)	−0.0014 (6)	−0.0065 (7)
C12	0.0263 (7)	0.0354 (8)	0.0407 (8)	−0.0018 (6)	−0.0038 (6)	−0.0006 (7)
C13	0.0233 (7)	0.0430 (10)	0.0480 (9)	0.0009 (6)	0.0005 (6)	−0.0063 (7)
C14	0.0281 (8)	0.0375 (9)	0.0482 (9)	0.0011 (6)	−0.0001 (6)	−0.0074 (7)
C15	0.0436 (11)	0.0745 (15)	0.0794 (14)	0.0136 (10)	0.0079 (10)	−0.0270 (12)
C16	0.0519 (13)	0.0620 (14)	0.1007 (19)	−0.0047 (10)	−0.0152 (12)	0.0040 (13)

F1—C5	1.355 (2)	C4—H4A	0.9300
N1—C8	1.342 (2)	C5—C6	1.374 (3)
N1—N2	1.3809 (19)	C6—H6	0.9300
N1—H1	0.910 (10)	C7—H7	0.9300
N2—C7	1.269 (2)	C8—C9	1.481 (2)
O1—C12	1.3465 (19)	C9—C14	1.388 (2)
O1—H1A	0.8200	C9—C10	1.401 (2)
O2—C11	1.364 (2)	C10—C11	1.380 (2)
O2—C15	1.425 (2)	C10—H10	0.9300
O3—C8	1.2456 (19)	C11—C12	1.408 (2)
O4—C16	1.388 (3)	C12—C13	1.382 (2)
O4—H4	0.8200	C13—C14	1.381 (2)
C1—C2	1.390 (3)	C13—H13	0.9300
C1—C6	1.397 (2)	C14—H14	0.9300
C1—C7	1.466 (2)	C15—H15A	0.9600
C2—C3	1.382 (3)	C15—H15B	0.9600
C2—H2	0.9300	C15—H15C	0.9600
C3—C4	1.378 (3)	C16—H16A	0.9600
C3—H3	0.9300	C16—H16B	0.9600
C4—C5	1.373 (3)	C16—H16C	0.9600
C8—N1—N2	117.91 (13)	C14—C9—C10	119.18 (14)
C8—N1—H1	121.0 (17)	C14—C9—C8	123.21 (15)
N2—N1—H1	121.0 (17)	C10—C9—C8	117.57 (14)
C7—N2—N1	116.24 (14)	C11—C10—C9	120.62 (14)
C12—O1—H1A	109.5	C11—C10—H10	119.7
C11—O2—C15	117.69 (14)	C9—C10—H10	119.7
C16—O4—H4	109.5	O2—C11—C10	125.62 (14)
C2—C1—C6	119.33 (16)	O2—C11—C12	114.55 (14)
C2—C1—C7	119.46 (16)	C10—C11—C12	119.83 (15)
C6—C1—C7	121.18 (16)	O1—C12—C13	123.90 (14)
C3—C2—C1	120.74 (18)	O1—C12—C11	117.05 (14)
C3—C2—H2	119.6	C13—C12—C11	119.04 (14)
C1—C2—H2	119.6	C14—C13—C12	121.15 (14)
C4—C3—C2	120.40 (19)	C14—C13—H13	119.4
C4—C3—H3	119.8	C12—C13—H13	119.4
C2—C3—H3	119.8	C13—C14—C9	120.15 (15)
C5—C4—C3	117.95 (18)	C13—C14—H14	119.9
C5—C4—H4A	121.0	C9—C14—H14	119.9
C3—C4—H4A	121.0	O2—C15—H15A	109.5
F1—C5—C4	117.99 (17)	O2—C15—H15B	109.5
F1—C5—C6	118.35 (18)	H15A—C15—H15B	109.5
C4—C5—C6	123.66 (19)	O2—C15—H15C	109.5
C5—C6—C1	117.91 (17)	H15A—C15—H15C	109.5
C5—C6—H6	121.0	H15B—C15—H15C	109.5
C1—C6—H6	121.0	O4—C16—H16A	109.5
N2—C7—C1	120.97 (15)	O4—C16—H16B	109.5
N2—C7—H7	119.5	H16A—C16—H16B	109.5
C1—C7—H7	119.5	O4—C16—H16C	109.5
O3—C8—N1	120.98 (15)	H16A—C16—H16C	109.5
O3—C8—C9	121.10 (15)	H16B—C16—H16C	109.5
N1—C8—C9	117.89 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4i	0.91 (1)	2.03 (1)	2.916 (2)	164 (2)
O4—H4···O3	0.82	1.95	2.772 (2)	176
O1—H1A···O3ii	0.82	1.94	2.7504 (17)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4i	0.91 (1)	2.03 (1)	2.916 (2)	164 (2)
O4—H4⋯O3	0.82	1.95	2.772 (2)	176
O1—H1A⋯O3ii	0.82	1.94	2.7504 (17)	168

Symmetry codes: (i) ; (ii) .