2-Fluoro-N'-(2-meth-oxy-benzyl-idene)benzohydrazide.

The mol-ecule of the title compound, C(15)H(13)FN(2)O(2), exists in a trans configuration with respect to the methyl-idene unit. The two benzene rings form a dihedral angle of of 64.7 (2)°. In the crystal, mol-ecules are linked through N-H⋯O hydrogen bonds into chains propagating along the c axis.

Related literature

For the reference bond lengths, see: Allen et al. (1987 ▶). For structural studies of hydrazone compounds, see: Han & Zhao (2010 ▶); Zhou & Yang (2010 ▶); Huang & Wu (2010 ▶); Shalash et al. (2010 ▶). For a related structure, see: Xu et al. (2011 ▶).

Experimental

Crystal data

C15H13FN2O2

M = 272.27

Monoclinic,

a = 13.612 (2) Å

b = 12.278 (2) Å

c = 7.925 (1) Å

β = 92.802 (3)°

V = 1322.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.17 × 0.13 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.983, T max = 0.988

10047 measured reflections

2821 independent reflections

1643 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.164

S = 1.03

2821 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536810050853/cv5011sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050853/cv5011Isup2.hkl

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

C15H13FN2O2	F(000) = 568
Mr = 272.27	Dx = 1.367 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1625 reflections
a = 13.612 (2) Å	θ = 2.2–26.4°
b = 12.278 (2) Å	µ = 0.10 mm−1
c = 7.925 (1) Å	T = 298 K
β = 92.802 (3)°	Block, colorless
V = 1322.9 (3) Å3	0.17 × 0.13 × 0.12 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2821 independent reflections
Radiation source: fine-focus sealed tube	1643 reflections with I > 2σ(I)
graphite	Rint = 0.047
ω scans	θmax = 27.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→16
Tmin = 0.983, Tmax = 0.988	k = −15→15
10047 measured reflections	l = −10→10

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0839P)2] where P = (Fo2 + 2Fc2)/3
2821 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.26 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	0.89639 (10)	0.58503 (11)	0.9614 (2)	0.0657 (5)
N1	0.72769 (12)	0.71726 (15)	0.9490 (2)	0.0409 (5)
H1	0.7427	0.6742	0.8687	0.049*
N2	0.63391 (12)	0.71379 (15)	1.0089 (2)	0.0392 (5)
O1	0.77942 (11)	0.85629 (12)	1.1218 (2)	0.0442 (4)
O2	0.43863 (11)	0.55230 (14)	0.7104 (2)	0.0561 (5)
C1	0.89489 (15)	0.77601 (18)	0.9435 (3)	0.0369 (5)
C2	0.94195 (16)	0.67840 (18)	0.9204 (3)	0.0414 (6)
C3	1.03448 (17)	0.6706 (2)	0.8625 (3)	0.0546 (7)
H3	1.0642	0.6030	0.8504	0.065*
C4	1.08295 (18)	0.7651 (3)	0.8224 (4)	0.0603 (8)
H4	1.1458	0.7614	0.7817	0.072*
C5	1.03917 (19)	0.8636 (2)	0.8423 (4)	0.0615 (8)
H5	1.0721	0.9269	0.8143	0.074*
C6	0.94636 (17)	0.8701 (2)	0.9034 (3)	0.0508 (7)
H6	0.9177	0.9379	0.9182	0.061*
C7	0.79557 (15)	0.78675 (18)	1.0143 (3)	0.0367 (6)
C8	0.57425 (15)	0.65389 (18)	0.9208 (3)	0.0384 (6)
H8	0.5954	0.6201	0.8240	0.046*
C9	0.47321 (15)	0.63784 (17)	0.9704 (3)	0.0376 (6)
C10	0.40509 (16)	0.58424 (17)	0.8620 (3)	0.0418 (6)
C11	0.31043 (16)	0.56584 (19)	0.9121 (4)	0.0504 (7)
H11	0.2652	0.5297	0.8403	0.061*
C12	0.28342 (17)	0.6008 (2)	1.0670 (4)	0.0591 (8)
H12	0.2197	0.5881	1.0996	0.071*
C13	0.34873 (18)	0.6544 (2)	1.1753 (4)	0.0607 (8)
H13	0.3295	0.6781	1.2801	0.073*
C14	0.44315 (17)	0.6725 (2)	1.1266 (3)	0.0500 (7)
H14	0.4876	0.7086	1.1998	0.060*
C15	0.3743 (2)	0.4906 (3)	0.6007 (4)	0.0838 (10)
H15A	0.3546	0.4257	0.6575	0.126*
H15B	0.4076	0.4711	0.5010	0.126*
H15C	0.3172	0.5333	0.5694	0.126*

	U11	U22	U33	U12	U13	U23
F1	0.0498 (9)	0.0509 (9)	0.0966 (13)	−0.0034 (7)	0.0045 (8)	0.0114 (9)
N1	0.0280 (10)	0.0526 (12)	0.0425 (12)	−0.0043 (8)	0.0072 (9)	−0.0084 (9)
N2	0.0299 (10)	0.0461 (11)	0.0420 (12)	−0.0021 (8)	0.0045 (9)	0.0006 (9)
O1	0.0435 (9)	0.0482 (9)	0.0412 (10)	−0.0005 (7)	0.0046 (8)	−0.0040 (8)
O2	0.0504 (10)	0.0698 (12)	0.0480 (11)	−0.0142 (9)	0.0016 (9)	−0.0147 (9)
C1	0.0306 (11)	0.0478 (13)	0.0323 (13)	−0.0031 (10)	0.0004 (10)	0.0015 (11)
C2	0.0331 (13)	0.0460 (14)	0.0449 (15)	−0.0051 (11)	−0.0007 (11)	0.0034 (12)
C3	0.0377 (14)	0.0665 (17)	0.0593 (18)	0.0072 (12)	0.0019 (13)	−0.0005 (14)
C4	0.0358 (14)	0.083 (2)	0.0631 (19)	−0.0034 (14)	0.0111 (13)	0.0023 (16)
C5	0.0482 (16)	0.0693 (19)	0.068 (2)	−0.0163 (14)	0.0163 (14)	0.0086 (16)
C6	0.0441 (14)	0.0538 (15)	0.0550 (17)	−0.0073 (12)	0.0078 (13)	0.0024 (13)
C7	0.0349 (12)	0.0434 (13)	0.0319 (13)	−0.0011 (10)	0.0016 (10)	0.0050 (11)
C8	0.0322 (12)	0.0444 (13)	0.0387 (14)	0.0013 (10)	0.0029 (10)	0.0020 (11)
C9	0.0313 (12)	0.0347 (12)	0.0470 (15)	0.0000 (9)	0.0021 (11)	0.0021 (11)
C10	0.0393 (13)	0.0362 (13)	0.0497 (16)	−0.0007 (10)	0.0009 (12)	−0.0001 (11)
C11	0.0333 (13)	0.0487 (15)	0.069 (2)	−0.0054 (11)	−0.0012 (13)	−0.0069 (13)
C12	0.0325 (13)	0.0613 (16)	0.085 (2)	−0.0047 (12)	0.0172 (14)	−0.0060 (16)
C13	0.0435 (15)	0.0712 (18)	0.069 (2)	−0.0037 (13)	0.0179 (14)	−0.0168 (16)
C14	0.0390 (14)	0.0585 (16)	0.0531 (17)	−0.0051 (11)	0.0087 (12)	−0.0129 (13)
C15	0.080 (2)	0.112 (3)	0.059 (2)	−0.0263 (19)	−0.0072 (17)	−0.0299 (19)

F1—C2	1.351 (2)	C5—H5	0.9300
N1—C7	1.343 (3)	C6—H6	0.9300
N1—N2	1.384 (2)	C8—C9	1.462 (3)
N1—H1	0.8600	C8—H8	0.9300
N2—C8	1.278 (3)	C9—C14	1.390 (3)
O1—C7	1.234 (3)	C9—C10	1.397 (3)
O2—C10	1.364 (3)	C10—C11	1.385 (3)
O2—C15	1.422 (3)	C11—C12	1.368 (4)
C1—C2	1.375 (3)	C11—H11	0.9300
C1—C6	1.395 (3)	C12—C13	1.373 (4)
C1—C7	1.495 (3)	C12—H12	0.9300
C2—C3	1.365 (3)	C13—C14	1.378 (3)
C3—C4	1.379 (4)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.361 (4)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C5—C6	1.377 (3)	C15—H15C	0.9600
C7—N1—N2	121.09 (19)	N2—C8—H8	119.6
C7—N1—H1	119.5	C9—C8—H8	119.6
N2—N1—H1	119.5	C14—C9—C10	118.4 (2)
C8—N2—N1	113.74 (19)	C14—C9—C8	121.3 (2)
C10—O2—C15	117.99 (19)	C10—C9—C8	120.2 (2)
C2—C1—C6	116.6 (2)	O2—C10—C11	124.2 (2)
C2—C1—C7	124.2 (2)	O2—C10—C9	115.86 (19)
C6—C1—C7	119.1 (2)	C11—C10—C9	120.0 (2)
F1—C2—C3	117.6 (2)	C12—C11—C10	120.0 (2)
F1—C2—C1	119.0 (2)	C12—C11—H11	120.0
C3—C2—C1	123.3 (2)	C10—C11—H11	120.0
C2—C3—C4	118.6 (2)	C11—C12—C13	121.1 (2)
C2—C3—H3	120.7	C11—C12—H12	119.4
C4—C3—H3	120.7	C13—C12—H12	119.4
C5—C4—C3	120.3 (2)	C12—C13—C14	119.1 (3)
C5—C4—H4	119.9	C12—C13—H13	120.4
C3—C4—H4	119.9	C14—C13—H13	120.4
C4—C5—C6	120.4 (2)	C13—C14—C9	121.3 (2)
C4—C5—H5	119.8	C13—C14—H14	119.4
C6—C5—H5	119.8	C9—C14—H14	119.4
C5—C6—C1	120.8 (2)	O2—C15—H15A	109.5
C5—C6—H6	119.6	O2—C15—H15B	109.5
C1—C6—H6	119.6	H15A—C15—H15B	109.5
O1—C7—N1	124.29 (19)	O2—C15—H15C	109.5
O1—C7—C1	121.0 (2)	H15A—C15—H15C	109.5
N1—C7—C1	114.7 (2)	H15B—C15—H15C	109.5
N2—C8—C9	120.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.08	2.866 (2)	152.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.08	2.866 (2)	152

Symmetry code: (i) .