N'-(5-Chloro-2-hy-droxy-benzyl-idene)-4-meth-oxy-benzohydrazide.

The asymmetric unit of the title compound, C(15)H(13)ClN(2)O(3), contains two independent hydrazone mol-ecules. Each mol-ecule adopts an E configuration with respect to the methyl-idene unit and forms an intra-molecular O-H⋯N hydrogen bond. The principal difference between the two unique mol-ecules is the relative orientation of the two benzene rings, the dihedral angles between them being 4.0 (3) and 65.9 (3)°, respectively. In the crystal, mol-ecules are linked through N-H⋯O hydrogen bonds, forming chains running along the c axis.

Related literature

For similar hydrazone derivatives, see: Li (2012 ▶); Zhu et al. (2012 ▶); Shen et al. (2012 ▶); Liu et al. (2011 ▶); Lei (2011 ▶).

Experimental

Crystal data

C15H13ClN2O3

M = 304.72

Monoclinic,

a = 17.569 (3) Å

b = 8.367 (2) Å

c = 19.454 (3) Å

β = 93.683 (3)°

V = 2853.8 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.28 mm−1

T = 298 K

0.11 × 0.08 × 0.07 mm

Data collection

Bruker SMART CCD area detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.970, T max = 0.981

11127 measured reflections

3752 independent reflections

2545 reflections with I > 2σ(I)

R int = 0.031

θmax = 22.7°

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.105

S = 1.02

3752 reflections

389 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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/S1600536812010707/sj5210sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010707/sj5210Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812010707/sj5210Isup3.cml

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

C15H13ClN2O3	F(000) = 1264
Mr = 304.72	Dx = 1.418 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2580 reflections
a = 17.569 (3) Å	θ = 2.3–24.1°
b = 8.367 (2) Å	µ = 0.28 mm−1
c = 19.454 (3) Å	T = 298 K
β = 93.683 (3)°	Cut from a needle, colorless
V = 2853.8 (9) Å3	0.11 × 0.08 × 0.07 mm
Z = 8

Bruker SMART CCD area detector diffractometer	3752 independent reflections
Radiation source: fine-focus sealed tube	2545 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω scans	θmax = 22.7°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −18→18
Tmin = 0.970, Tmax = 0.981	k = −7→9
11127 measured reflections	l = −21→20

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0449P)2 + 0.5824P] where P = (Fo2 + 2Fc2)/3
3752 reflections	(Δ/σ)max = 0.001
389 parameters	Δρmax = 0.15 e Å−3
2 restraints	Δρmin = −0.23 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	0.43413 (5)	0.26184 (11)	0.43593 (6)	0.1157 (4)
Cl2	0.46637 (5)	0.46291 (14)	0.15497 (6)	0.1363 (4)
N1	0.14645 (12)	0.6342 (2)	0.52429 (10)	0.0574 (5)
N2	0.07370 (12)	0.6759 (3)	0.50355 (10)	0.0576 (6)
N3	0.15526 (12)	0.6563 (2)	0.26936 (11)	0.0604 (6)
N4	0.07935 (12)	0.6606 (3)	0.24935 (10)	0.0600 (6)
O1	0.25873 (11)	0.6596 (3)	0.61141 (10)	0.0842 (6)
H1	0.2159	0.6780	0.5939	0.126*
O2	0.06353 (10)	0.7996 (2)	0.60402 (9)	0.0713 (5)
O3	−0.26093 (11)	0.9580 (2)	0.46447 (10)	0.0847 (6)
O4	0.26641 (13)	0.7120 (3)	0.35609 (11)	0.1122 (8)
H4	0.2214	0.7009	0.3429	0.168*
O5	0.04802 (10)	0.6214 (2)	0.35756 (9)	0.0716 (5)
O6	−0.27527 (11)	0.6996 (3)	0.19814 (10)	0.0878 (6)
C1	0.26287 (14)	0.5095 (3)	0.50765 (14)	0.0598 (7)
C2	0.29662 (16)	0.5671 (3)	0.56912 (15)	0.0680 (8)
C3	0.37158 (18)	0.5317 (4)	0.58736 (17)	0.0892 (10)
H3	0.3944	0.5729	0.6280	0.107*
C4	0.41271 (18)	0.4375 (4)	0.5469 (2)	0.0911 (10)
H4A	0.4631	0.4129	0.5602	0.109*
C5	0.38012 (16)	0.3790 (4)	0.48679 (18)	0.0792 (9)
C6	0.30662 (15)	0.4144 (3)	0.46739 (15)	0.0732 (8)
H6	0.2851	0.3739	0.4261	0.088*
C7	0.18546 (14)	0.5496 (3)	0.48577 (14)	0.0610 (7)
H7	0.1643	0.5136	0.4436	0.073*
C8	0.03506 (14)	0.7664 (3)	0.54710 (14)	0.0549 (6)
C9	−0.04190 (14)	0.8190 (3)	0.52330 (12)	0.0517 (6)
C10	−0.07920 (15)	0.7694 (3)	0.46248 (13)	0.0648 (7)
H10	−0.0546	0.7010	0.4334	0.078*
C11	−0.15120 (16)	0.8190 (3)	0.44458 (14)	0.0700 (8)
H11	−0.1753	0.7849	0.4032	0.084*
C12	−0.18882 (16)	0.9187 (3)	0.48663 (14)	0.0635 (7)
C13	−0.15250 (16)	0.9716 (3)	0.54685 (13)	0.0663 (7)
H13	−0.1770	1.0408	0.5756	0.080*
C14	−0.08003 (15)	0.9212 (3)	0.56394 (13)	0.0637 (7)
H14	−0.0555	0.9576	0.6048	0.076*
C15	−0.30577 (17)	1.0475 (4)	0.50860 (17)	0.0905 (10)
H15A	−0.3096	0.9908	0.5511	0.136*
H15B	−0.3559	1.0628	0.4869	0.136*
H15C	−0.2823	1.1496	0.5177	0.136*
C16	0.28167 (14)	0.6057 (3)	0.24456 (14)	0.0608 (7)
C17	0.31081 (17)	0.6535 (4)	0.30840 (17)	0.0820 (9)
C18	0.3881 (2)	0.6417 (5)	0.3241 (2)	0.1183 (14)
H18	0.4081	0.6743	0.3672	0.142*
C19	0.4352 (2)	0.5837 (5)	0.2780 (2)	0.1143 (13)
H19	0.4873	0.5763	0.2896	0.137*
C20	0.40683 (16)	0.5361 (4)	0.21483 (19)	0.0863 (10)
C21	0.33051 (15)	0.5475 (3)	0.19787 (15)	0.0730 (8)
H21	0.3112	0.5156	0.1544	0.088*
C22	0.20133 (15)	0.6144 (3)	0.22551 (14)	0.0623 (7)
H22	0.1833	0.5891	0.1809	0.075*
C23	0.02814 (14)	0.6472 (3)	0.29745 (14)	0.0549 (6)
C24	−0.05182 (14)	0.6598 (3)	0.27157 (12)	0.0520 (6)
C25	−0.10656 (15)	0.5695 (3)	0.30053 (13)	0.0618 (7)
H25	−0.0924	0.5008	0.3367	0.074*
C26	−0.18192 (15)	0.5784 (3)	0.27714 (14)	0.0661 (7)
H26	−0.2182	0.5148	0.2968	0.079*
C27	−0.20315 (15)	0.6807 (3)	0.22506 (14)	0.0617 (7)
C28	−0.14915 (16)	0.7721 (3)	0.19611 (14)	0.0664 (7)
H28	−0.1637	0.8429	0.1608	0.080*
C29	−0.07463 (14)	0.7606 (3)	0.21823 (13)	0.0584 (7)
H29	−0.0385	0.8215	0.1972	0.070*
C30	−0.33470 (17)	0.6190 (5)	0.23012 (19)	0.1119 (12)
H30A	−0.3272	0.5057	0.2270	0.168*
H30B	−0.3829	0.6472	0.2073	0.168*
H30C	−0.3342	0.6498	0.2777	0.168*
H2	0.0577 (14)	0.658 (3)	0.4600 (7)	0.080*
H4B	0.0664 (14)	0.662 (3)	0.2044 (6)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.0708 (6)	0.1124 (7)	0.1654 (10)	0.0061 (5)	0.0199 (5)	−0.0250 (6)
Cl2	0.0713 (6)	0.1579 (10)	0.1830 (11)	0.0187 (6)	0.0332 (6)	0.0071 (8)
N1	0.0566 (14)	0.0641 (14)	0.0509 (13)	−0.0031 (11)	0.0003 (11)	0.0036 (11)
N2	0.0580 (14)	0.0720 (15)	0.0426 (13)	−0.0007 (11)	0.0009 (11)	−0.0018 (12)
N3	0.0559 (14)	0.0726 (15)	0.0522 (14)	−0.0024 (11)	−0.0008 (11)	0.0058 (12)
N4	0.0553 (14)	0.0812 (16)	0.0432 (13)	0.0033 (11)	0.0002 (11)	0.0041 (12)
O1	0.0845 (14)	0.1094 (17)	0.0571 (12)	−0.0066 (13)	−0.0066 (10)	−0.0078 (12)
O2	0.0685 (12)	0.0989 (14)	0.0459 (11)	−0.0023 (10)	−0.0005 (9)	−0.0081 (10)
O3	0.0774 (14)	0.0921 (15)	0.0832 (14)	0.0190 (11)	−0.0061 (11)	−0.0025 (12)
O4	0.0952 (17)	0.176 (2)	0.0638 (14)	−0.0141 (17)	−0.0116 (13)	−0.0161 (15)
O5	0.0738 (12)	0.1003 (15)	0.0402 (11)	0.0095 (10)	0.0010 (9)	−0.0005 (10)
O6	0.0610 (13)	0.1084 (16)	0.0922 (15)	0.0039 (11)	−0.0086 (11)	0.0064 (12)
C1	0.0575 (17)	0.0615 (17)	0.0598 (18)	−0.0100 (14)	0.0004 (14)	0.0032 (14)
C2	0.069 (2)	0.076 (2)	0.0587 (19)	−0.0064 (15)	0.0001 (16)	0.0029 (16)
C3	0.073 (2)	0.113 (3)	0.078 (2)	−0.011 (2)	−0.0167 (18)	0.006 (2)
C4	0.062 (2)	0.102 (3)	0.107 (3)	−0.0021 (19)	−0.010 (2)	0.015 (2)
C5	0.0587 (19)	0.077 (2)	0.102 (3)	−0.0065 (15)	0.0061 (17)	−0.0010 (19)
C6	0.0585 (18)	0.077 (2)	0.083 (2)	−0.0081 (15)	0.0012 (16)	−0.0086 (17)
C7	0.0579 (17)	0.0694 (18)	0.0554 (17)	−0.0076 (14)	0.0006 (14)	−0.0057 (15)
C8	0.0615 (17)	0.0606 (17)	0.0430 (16)	−0.0097 (13)	0.0067 (14)	0.0054 (14)
C9	0.0626 (17)	0.0521 (15)	0.0409 (15)	−0.0071 (13)	0.0079 (13)	0.0046 (12)
C10	0.0662 (18)	0.0723 (19)	0.0554 (18)	0.0018 (14)	0.0006 (14)	−0.0087 (14)
C11	0.075 (2)	0.0770 (19)	0.0571 (18)	0.0035 (16)	−0.0060 (15)	−0.0107 (15)
C12	0.0667 (19)	0.0624 (18)	0.0609 (19)	0.0016 (14)	0.0005 (15)	0.0101 (15)
C13	0.081 (2)	0.0647 (18)	0.0543 (18)	0.0082 (15)	0.0094 (15)	0.0012 (14)
C14	0.074 (2)	0.0667 (18)	0.0499 (17)	−0.0009 (15)	0.0025 (14)	0.0029 (14)
C15	0.081 (2)	0.089 (2)	0.102 (3)	0.0167 (18)	0.0116 (19)	0.006 (2)
C16	0.0530 (17)	0.0727 (18)	0.0556 (18)	−0.0054 (13)	−0.0043 (14)	0.0155 (15)
C17	0.067 (2)	0.110 (3)	0.067 (2)	−0.0139 (18)	−0.0104 (17)	0.0100 (19)
C18	0.076 (3)	0.182 (4)	0.093 (3)	−0.019 (3)	−0.026 (2)	0.008 (3)
C19	0.058 (2)	0.153 (4)	0.128 (4)	−0.011 (2)	−0.021 (2)	0.025 (3)
C20	0.0536 (19)	0.097 (2)	0.108 (3)	0.0026 (16)	0.0074 (19)	0.026 (2)
C21	0.0596 (19)	0.084 (2)	0.075 (2)	−0.0016 (15)	−0.0003 (16)	0.0158 (17)
C22	0.0597 (17)	0.0742 (19)	0.0520 (17)	−0.0034 (14)	−0.0034 (14)	0.0081 (14)
C23	0.0652 (18)	0.0570 (16)	0.0426 (16)	0.0010 (13)	0.0037 (14)	−0.0039 (13)
C24	0.0594 (16)	0.0518 (16)	0.0451 (15)	0.0052 (13)	0.0059 (12)	−0.0032 (13)
C25	0.0703 (19)	0.0636 (18)	0.0516 (17)	0.0030 (14)	0.0035 (14)	0.0052 (14)
C26	0.0650 (19)	0.0663 (19)	0.0678 (19)	−0.0045 (14)	0.0088 (15)	−0.0001 (16)
C27	0.0582 (18)	0.0659 (18)	0.0603 (18)	0.0050 (15)	−0.0009 (14)	−0.0055 (15)
C28	0.0682 (19)	0.0692 (19)	0.0612 (18)	0.0134 (15)	−0.0009 (15)	0.0100 (15)
C29	0.0637 (18)	0.0559 (16)	0.0561 (17)	0.0043 (13)	0.0089 (13)	0.0049 (14)
C30	0.060 (2)	0.139 (3)	0.137 (3)	−0.012 (2)	0.006 (2)	0.009 (3)

Cl1—C5	1.721 (3)	C10—H10	0.9300
Cl2—C20	1.727 (3)	C11—C12	1.368 (4)
N1—C7	1.264 (3)	C11—H11	0.9300
N1—N2	1.361 (3)	C12—C13	1.371 (4)
N2—C8	1.351 (3)	C13—C14	1.362 (3)
N2—H2	0.888 (10)	C13—H13	0.9300
N3—C22	1.263 (3)	C14—H14	0.9300
N3—N4	1.366 (3)	C15—H15A	0.9600
N4—C23	1.344 (3)	C15—H15B	0.9600
N4—H4B	0.889 (10)	C15—H15C	0.9600
O1—C2	1.338 (3)	C16—C17	1.372 (4)
O1—H1	0.8200	C16—C21	1.378 (4)
O2—C8	1.217 (3)	C16—C22	1.438 (3)
O3—C12	1.352 (3)	C17—C18	1.375 (4)
O3—C15	1.416 (3)	C18—C19	1.350 (5)
O4—C17	1.343 (4)	C18—H18	0.9300
O4—H4	0.8200	C19—C20	1.356 (5)
O5—C23	1.218 (3)	C19—H19	0.9300
O6—C27	1.349 (3)	C20—C21	1.364 (4)
O6—C30	1.420 (3)	C21—H21	0.9300
C1—C6	1.383 (4)	C22—H22	0.9300
C1—C2	1.387 (4)	C23—C24	1.465 (3)
C1—C7	1.438 (3)	C24—C25	1.372 (3)
C2—C3	1.374 (4)	C24—C29	1.377 (3)
C3—C4	1.355 (4)	C25—C26	1.374 (3)
C3—H3	0.9300	C25—H25	0.9300
C4—C5	1.359 (4)	C26—C27	1.360 (4)
C4—H4A	0.9300	C26—H26	0.9300
C5—C6	1.355 (4)	C27—C28	1.368 (4)
C6—H6	0.9300	C28—C29	1.355 (3)
C7—H7	0.9300	C28—H28	0.9300
C8—C9	1.469 (3)	C29—H29	0.9300
C9—C14	1.368 (3)	C30—H30A	0.9600
C9—C10	1.379 (3)	C30—H30B	0.9600
C10—C11	1.356 (3)	C30—H30C	0.9600
C7—N1—N2	120.2 (2)	O3—C15—H15A	109.5
C8—N2—N1	117.2 (2)	O3—C15—H15B	109.5
C8—N2—H2	123.6 (17)	H15A—C15—H15B	109.5
N1—N2—H2	118.2 (17)	O3—C15—H15C	109.5
C22—N3—N4	118.1 (2)	H15A—C15—H15C	109.5
C23—N4—N3	119.0 (2)	H15B—C15—H15C	109.5
C23—N4—H4B	123.0 (17)	C17—C16—C21	119.2 (3)
N3—N4—H4B	117.7 (17)	C17—C16—C22	121.4 (3)
C2—O1—H1	109.5	C21—C16—C22	119.4 (3)
C12—O3—C15	118.8 (2)	O4—C17—C16	122.2 (3)
C17—O4—H4	109.5	O4—C17—C18	118.8 (3)
C27—O6—C30	118.2 (2)	C16—C17—C18	119.0 (3)
C6—C1—C2	117.8 (3)	C19—C18—C17	121.2 (4)
C6—C1—C7	121.1 (3)	C19—C18—H18	119.4
C2—C1—C7	121.2 (3)	C17—C18—H18	119.4
O1—C2—C3	118.2 (3)	C18—C19—C20	120.1 (3)
O1—C2—C1	122.0 (3)	C18—C19—H19	119.9
C3—C2—C1	119.8 (3)	C20—C19—H19	119.9
C4—C3—C2	120.9 (3)	C19—C20—C21	119.9 (3)
C4—C3—H3	119.6	C19—C20—Cl2	120.8 (3)
C2—C3—H3	119.6	C21—C20—Cl2	119.4 (3)
C3—C4—C5	119.9 (3)	C20—C21—C16	120.6 (3)
C3—C4—H4A	120.1	C20—C21—H21	119.7
C5—C4—H4A	120.1	C16—C21—H21	119.7
C6—C5—C4	120.1 (3)	N3—C22—C16	120.1 (2)
C6—C5—Cl1	121.0 (3)	N3—C22—H22	120.0
C4—C5—Cl1	118.8 (3)	C16—C22—H22	120.0
C5—C6—C1	121.5 (3)	O5—C23—N4	121.3 (2)
C5—C6—H6	119.3	O5—C23—C24	123.5 (2)
C1—C6—H6	119.3	N4—C23—C24	115.1 (2)
N1—C7—C1	119.6 (2)	C25—C24—C29	118.0 (2)
N1—C7—H7	120.2	C25—C24—C23	120.1 (2)
C1—C7—H7	120.2	C29—C24—C23	121.9 (2)
O2—C8—N2	120.3 (2)	C24—C25—C26	121.3 (2)
O2—C8—C9	122.3 (2)	C24—C25—H25	119.3
N2—C8—C9	117.4 (2)	C26—C25—H25	119.3
C14—C9—C10	117.4 (2)	C27—C26—C25	119.5 (3)
C14—C9—C8	118.7 (2)	C27—C26—H26	120.2
C10—C9—C8	123.9 (2)	C25—C26—H26	120.2
C11—C10—C9	120.8 (3)	O6—C27—C26	124.7 (3)
C11—C10—H10	119.6	O6—C27—C28	115.7 (3)
C9—C10—H10	119.6	C26—C27—C28	119.6 (2)
C10—C11—C12	120.8 (3)	C29—C28—C27	120.8 (3)
C10—C11—H11	119.6	C29—C28—H28	119.6
C12—C11—H11	119.6	C27—C28—H28	119.6
O3—C12—C11	115.9 (3)	C28—C29—C24	120.8 (2)
O3—C12—C13	124.7 (3)	C28—C29—H29	119.6
C11—C12—C13	119.4 (3)	C24—C29—H29	119.6
C14—C13—C12	119.0 (3)	O6—C30—H30A	109.5
C14—C13—H13	120.5	O6—C30—H30B	109.5
C12—C13—H13	120.5	H30A—C30—H30B	109.5
C13—C14—C9	122.5 (3)	O6—C30—H30C	109.5
C13—C14—H14	118.8	H30A—C30—H30C	109.5
C9—C14—H14	118.8	H30B—C30—H30C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···O2i	0.89 (1)	1.98 (1)	2.843 (3)	164 (2)
N2—H2···O5	0.89 (1)	2.01 (1)	2.883 (3)	166 (2)
O4—H4···N3	0.82	1.82	2.540 (3)	145
O1—H1···N1	0.82	1.80	2.526 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4B⋯O2i	0.89 (1)	1.98 (1)	2.843 (3)	164 (2)
N2—H2⋯O5	0.89 (1)	2.01 (1)	2.883 (3)	166 (2)
O4—H4⋯N3	0.82	1.82	2.540 (3)	145
O1—H1⋯N1	0.82	1.80	2.526 (3)	146

Symmetry code: (i) .