2-Chloro-N'-(2-hydr-oxy-4-methoxy-benzyl-idene)benzohydrazide.

In the title compound, C(15)H(13)ClN(2)O(3), the dihedral angle between the two benzene rings is 82.09 (10)° and an intra-molecular O-H⋯N hydrogen bond occurs. In the crystal structure, N-H⋯O hydrogen bonds link mol-ecules into chains propagating in [100].

Related literature

For related structures, see: Fun et al. (2008 ▶); Ali et al. (2007 ▶); Zhi & Yang (2007 ▶).

Experimental

Crystal data

C15H13ClN2O3

M = 304.72

Triclinic,

a = 5.002 (1) Å

b = 10.866 (2) Å

c = 13.169 (3) Å

α = 83.946 (3)°

β = 81.721 (4)°

γ = 89.540 (3)°

V = 704.3 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.28 mm−1

T = 298 K

0.13 × 0.12 × 0.10 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.964, T max = 0.972

4214 measured reflections

3017 independent reflections

2342 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.117

S = 1.03

3017 reflections

195 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009659/hb2929sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009659/hb2929Isup2.hkl

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

C15H13ClN2O3	Z = 2
Mr = 304.72	F(000) = 316
Triclinic, P1	Dx = 1.437 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.002 (1) Å	Cell parameters from 1381 reflections
b = 10.866 (2) Å	θ = 2.3–26.1°
c = 13.169 (3) Å	µ = 0.28 mm−1
α = 83.946 (3)°	T = 298 K
β = 81.721 (4)°	Block, yellow
γ = 89.540 (3)°	0.13 × 0.12 × 0.10 mm
V = 704.3 (2) Å3

Bruker SMART 1000 CCD diffractometer	3017 independent reflections
Radiation source: fine-focus sealed tube	2342 reflections with I > 2σ(I)
graphite	Rint = 0.012
ω scans	θmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −6→6
Tmin = 0.964, Tmax = 0.972	k = −13→13
4214 measured reflections	l = −12→16

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) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0529P)2 + 0.2179P] where P = (Fo2 + 2Fc2)/3
3017 reflections	(Δ/σ)max < 0.001
195 parameters	Δρmax = 0.19 e Å−3
1 restraint	Δρmin = −0.28 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
Cl1	0.46805 (11)	0.16315 (5)	0.36552 (4)	0.05502 (19)
N1	−0.0337 (3)	0.45450 (15)	0.28647 (12)	0.0395 (4)
N2	0.0359 (3)	0.54868 (14)	0.20805 (12)	0.0398 (4)
O1	0.3975 (3)	0.44360 (13)	0.31753 (12)	0.0524 (4)
O2	0.3019 (3)	0.74949 (15)	0.13643 (11)	0.0581 (4)
H2	0.2626	0.6867	0.1759	0.087*
O3	0.1119 (3)	0.94970 (14)	−0.18396 (11)	0.0549 (4)
C1	0.0671 (4)	0.32016 (16)	0.43192 (14)	0.0348 (4)
C2	0.2007 (4)	0.20956 (17)	0.45277 (15)	0.0396 (4)
C3	0.1198 (5)	0.13155 (19)	0.54152 (17)	0.0521 (5)
H3	0.2105	0.0577	0.5543	0.063*
C4	−0.0949 (5)	0.1634 (2)	0.61080 (17)	0.0577 (6)
H4	−0.1477	0.1115	0.6710	0.069*
C5	−0.2326 (4)	0.2716 (2)	0.59178 (16)	0.0527 (5)
H5	−0.3786	0.2925	0.6388	0.063*
C6	−0.1531 (4)	0.34920 (18)	0.50246 (15)	0.0422 (4)
H6	−0.2480	0.4217	0.4894	0.051*
C7	0.1614 (3)	0.41011 (16)	0.34009 (14)	0.0357 (4)
C8	−0.1114 (4)	0.56612 (18)	0.13669 (15)	0.0415 (4)
H8	−0.2606	0.5153	0.1375	0.050*
C9	−0.0462 (4)	0.66529 (17)	0.05418 (14)	0.0383 (4)
C10	0.1562 (4)	0.75315 (18)	0.05729 (14)	0.0400 (4)
C11	0.2109 (4)	0.84952 (19)	−0.02082 (15)	0.0457 (5)
H11	0.3426	0.9082	−0.0171	0.055*
C12	0.0700 (4)	0.85834 (18)	−0.10403 (14)	0.0425 (5)
C13	−0.1288 (4)	0.7717 (2)	−0.10967 (16)	0.0488 (5)
H13	−0.2226	0.7771	−0.1660	0.059*
C14	−0.1851 (4)	0.67777 (19)	−0.03091 (15)	0.0460 (5)
H14	−0.3202	0.6207	−0.0345	0.055*
C15	0.3106 (5)	1.0415 (2)	−0.17935 (18)	0.0566 (6)
H15A	0.2643	1.0815	−0.1176	0.085*
H15B	0.3173	1.1018	−0.2385	0.085*
H15C	0.4840	1.0031	−0.1789	0.085*
H1	−0.205 (3)	0.427 (2)	0.300 (2)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.0551 (3)	0.0522 (3)	0.0583 (3)	0.0181 (2)	−0.0093 (2)	−0.0084 (2)
N1	0.0276 (8)	0.0432 (9)	0.0443 (9)	−0.0003 (6)	−0.0041 (7)	0.0097 (7)
N2	0.0331 (8)	0.0414 (9)	0.0420 (9)	0.0022 (6)	−0.0047 (7)	0.0083 (7)
O1	0.0245 (7)	0.0592 (9)	0.0677 (10)	−0.0014 (6)	−0.0054 (6)	0.0187 (7)
O2	0.0571 (9)	0.0685 (10)	0.0483 (9)	−0.0179 (8)	−0.0210 (7)	0.0156 (7)
O3	0.0616 (10)	0.0567 (9)	0.0430 (8)	0.0006 (7)	−0.0085 (7)	0.0118 (7)
C1	0.0308 (9)	0.0364 (9)	0.0379 (9)	−0.0023 (7)	−0.0092 (7)	−0.0006 (7)
C2	0.0392 (10)	0.0385 (10)	0.0429 (10)	0.0018 (8)	−0.0138 (8)	−0.0023 (8)
C3	0.0627 (14)	0.0394 (11)	0.0541 (13)	0.0000 (10)	−0.0184 (11)	0.0092 (9)
C4	0.0657 (15)	0.0581 (14)	0.0451 (12)	−0.0149 (11)	−0.0081 (11)	0.0158 (10)
C5	0.0485 (12)	0.0648 (14)	0.0419 (11)	−0.0100 (11)	0.0010 (9)	−0.0013 (10)
C6	0.0368 (10)	0.0439 (11)	0.0448 (11)	−0.0008 (8)	−0.0050 (8)	−0.0007 (8)
C7	0.0287 (9)	0.0351 (9)	0.0418 (10)	0.0021 (7)	−0.0035 (7)	0.0007 (7)
C8	0.0342 (10)	0.0437 (11)	0.0451 (11)	0.0025 (8)	−0.0052 (8)	0.0011 (8)
C9	0.0340 (9)	0.0414 (10)	0.0384 (10)	0.0079 (8)	−0.0045 (8)	−0.0012 (8)
C10	0.0365 (10)	0.0459 (11)	0.0361 (10)	0.0039 (8)	−0.0053 (8)	0.0022 (8)
C11	0.0427 (11)	0.0481 (11)	0.0438 (11)	−0.0017 (9)	−0.0044 (9)	0.0039 (9)
C12	0.0431 (11)	0.0450 (11)	0.0357 (10)	0.0107 (8)	−0.0002 (8)	0.0045 (8)
C13	0.0531 (13)	0.0533 (12)	0.0415 (11)	0.0070 (10)	−0.0161 (9)	−0.0002 (9)
C14	0.0446 (11)	0.0469 (11)	0.0473 (11)	0.0012 (9)	−0.0122 (9)	−0.0013 (9)
C15	0.0579 (14)	0.0532 (13)	0.0520 (13)	0.0003 (11)	0.0010 (10)	0.0131 (10)

Cl1—C2	1.741 (2)	C5—C6	1.384 (3)
N1—C7	1.343 (2)	C5—H5	0.9300
N1—N2	1.384 (2)	C6—H6	0.9300
N1—H1	0.897 (10)	C8—C9	1.451 (3)
N2—C8	1.273 (2)	C8—H8	0.9300
O1—C7	1.224 (2)	C9—C14	1.395 (3)
O2—C10	1.352 (2)	C9—C10	1.405 (3)
O2—H2	0.8200	C10—C11	1.388 (3)
O3—C12	1.363 (2)	C11—C12	1.381 (3)
O3—C15	1.426 (3)	C11—H11	0.9300
C1—C2	1.392 (3)	C12—C13	1.390 (3)
C1—C6	1.392 (3)	C13—C14	1.376 (3)
C1—C7	1.495 (2)	C13—H13	0.9300
C2—C3	1.382 (3)	C14—H14	0.9300
C3—C4	1.373 (3)	C15—H15A	0.9600
C3—H3	0.9300	C15—H15B	0.9600
C4—C5	1.376 (3)	C15—H15C	0.9600
C4—H4	0.9300
C7—N1—N2	117.48 (14)	N2—C8—C9	119.94 (18)
C7—N1—H1	123.4 (17)	N2—C8—H8	120.0
N2—N1—H1	119.1 (17)	C9—C8—H8	120.0
C8—N2—N1	118.57 (16)	C14—C9—C10	117.45 (18)
C10—O2—H2	109.5	C14—C9—C8	121.07 (18)
C12—O3—C15	117.32 (17)	C10—C9—C8	121.47 (17)
C2—C1—C6	118.04 (17)	O2—C10—C11	117.14 (17)
C2—C1—C7	122.16 (17)	O2—C10—C9	122.07 (17)
C6—C1—C7	119.72 (16)	C11—C10—C9	120.78 (18)
C3—C2—C1	121.08 (19)	C12—C11—C10	120.03 (19)
C3—C2—Cl1	118.05 (16)	C12—C11—H11	120.0
C1—C2—Cl1	120.83 (15)	C10—C11—H11	120.0
C4—C3—C2	119.7 (2)	O3—C12—C11	123.68 (19)
C4—C3—H3	120.1	O3—C12—C13	115.99 (18)
C2—C3—H3	120.1	C11—C12—C13	120.33 (18)
C3—C4—C5	120.49 (19)	C14—C13—C12	119.22 (18)
C3—C4—H4	119.8	C14—C13—H13	120.4
C5—C4—H4	119.8	C12—C13—H13	120.4
C4—C5—C6	119.8 (2)	C13—C14—C9	122.17 (19)
C4—C5—H5	120.1	C13—C14—H14	118.9
C6—C5—H5	120.1	C9—C14—H14	118.9
C5—C6—C1	120.87 (19)	O3—C15—H15A	109.5
C5—C6—H6	119.6	O3—C15—H15B	109.5
C1—C6—H6	119.6	H15A—C15—H15B	109.5
O1—C7—N1	122.63 (16)	O3—C15—H15C	109.5
O1—C7—C1	122.38 (16)	H15A—C15—H15C	109.5
N1—C7—C1	114.96 (15)	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.82	1.86	2.583 (2)	146
N1—H1···O1i	0.90 (1)	1.98 (1)	2.817 (2)	156 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2	0.82	1.86	2.583 (2)	146
N1—H1⋯O1i	0.897 (10)	1.976 (14)	2.817 (2)	156 (2)

Symmetry code: (i) .