2-Hydr­oxy-N′-[(1Z)-1-(2-hydr­oxy-5-methyl­phen­yl)-2-methyl­propyl­idene]benzohydrazide

Chang, J.-G.; Zhao, R.-G.

doi:10.1107/S160053680706357X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o197

https://doi.org/10.1107/S160053680706357X

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2-Hydroxy-N′-[(1Z)-1-(2-hydroxy-5-methylphenyl)-2-methylpropylidene]benzohydrazide

Jian-Guo Chang ^a ^* and Ren-Gao Zhao ^a

^aDepartment of Materials Science and Chemical Engineering, Taishan University, 271021 Taian, Shandong, People's Republic of China
^*Correspondence e-mail: tsucjg@163.com

(Received 13 November 2007; accepted 26 November 2007; online 6 December 2007)

The title compound, C₁₈H₂₀N₂O₃, adopts a cis conformation with respect to the C=N double bond. The crystal structure is stabilized by intramolecular N—H⋯O and intermolecular O—H⋯O hydrogen bonds.

Related literature

For further details of the chemistry of the title compound, see: Carcelli et al. (1995 ); Salem (1998 ).

Experimental

Crystal data

C₁₈H₂₀N₂O₃
M_r = 312.36
Monoclinic, P 2₁ /c
a = 11.2144 (11) Å
b = 11.2887 (11) Å
c = 13.6535 (13) Å
β = 107.000 (2)°
V = 1653.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 273 (2) K
0.25 × 0.22 × 0.16 mm

Data collection

Bruker APEX2 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.987, T_max = 0.991
8523 measured reflections
2924 independent reflections
2094 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.139
S = 1.00
2924 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2	0.86	1.98	2.6413 (18)	133
O2—H2⋯O1ⁱ	0.82	1.96	2.7249 (17)	155
O1—H1⋯O3ⁱⁱ	0.82	1.90	2.6787 (18)	158
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053680706357X/pk2070sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680706357X/pk2070Isup2.hkl

checkCIF report

Comment top

The chemistry of aroylhydrazones continues to attract much attention due to their ability to coordinate metal ions (Salem, 1998) and their biological activity (Carcelli et al., 1995). As an extension of work on the structural characterization of aroylhydrazone derivatives, the title compound was synthesized and its crystal structure is reported here.

The title molecule displays a cis conformation with respect to the C8=N2 double bond (Fig. 1). The dihedral angle between the two benzene rings is 75.01 (6)°. The crystal structure is stabilized by intramolecular N—H···O and intermolecular O—H···O hydrogen bonds (Table 1. and Fig. 2).

Related literature top

For further details of the chemistry of the title compound, see: Carcelli et al. (1995); Salem (1998).

Experimental top

2-hydroxybenzohydrazide (0.01 mol,1.52 g) was dissolved in anhydrous ethanol (50 ml) and 1-(2-hydroxy-5-methylphenyl)-2-methylpropan-1-one (0.01 mol, 1.78 g) was added. The reaction mixture was refluxed for 6 h with stirring, and the resulting precipitate was collected by filtration, washed several times with ethanol and dried in vacuo (yield 85%). The compound (1.0 mmol, 0.31 g) was dissolved in dimethylformamide (15 ml) and kept at room temperature for 30 d to obtain colourless single crystals suitable for X-ray diffraction.

Structure description top

For further details of the chemistry of the title compound, see: Carcelli et al. (1995); Salem (1998).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top

	Fig. 1. The molecular structure of the title compound showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A packing diagram showing intramolecular N—H···O and intermolecular O—H···O hydrogen bonds (dashed lines). H atoms not involved in hydrogen bonding have been omitted for clarity.

2-Hydroxy-N'-[(1Z)-1-(2-hydroxy-5-methylphenyl)-2- methylpropylidene]benzohydrazide top

Crystal data top

C₁₈H₂₀N₂O₃	F(000) = 664
M_r = 312.36	D_x = 1.255 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2019 reflections
a = 11.2144 (11) Å	θ = 2.6–23.2°
b = 11.2887 (11) Å	µ = 0.09 mm⁻¹
c = 13.6535 (13) Å	T = 273 K
β = 107.000 (2)°	Block, yellow
V = 1653.0 (3) Å³	0.25 × 0.22 × 0.16 mm
Z = 4

Data collection top

Bruker APEX2 CCD area-detector diffractometer	2924 independent reflections
Radiation source: fine-focus sealed tube	2094 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
φ and ω scans	θ_max = 25.1°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −13→10
T_min = 0.987, T_max = 0.991	k = −12→13
8523 measured reflections	l = −10→16

Refinement top

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0879P)²] where P = (F_o² + 2F_c²)/3
2924 reflections	(Δ/σ)_max < 0.001
210 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₈H₂₀N₂O₃	V = 1653.0 (3) Å³
M_r = 312.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.2144 (11) Å	µ = 0.09 mm⁻¹
b = 11.2887 (11) Å	T = 273 K
c = 13.6535 (13) Å	0.25 × 0.22 × 0.16 mm
β = 107.000 (2)°

Data collection top

Bruker APEX2 CCD area-detector diffractometer	2924 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2094 reflections with I > 2σ(I)
T_min = 0.987, T_max = 0.991	R_int = 0.026
8523 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 1.00	Δρ_max = 0.20 e Å⁻³
2924 reflections	Δρ_min = −0.15 e Å⁻³
210 parameters

Special details top

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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.14313 (13)	0.32510 (11)	0.31013 (11)	0.0609 (4)
H1	0.1500	0.3965	0.3215	0.091*
O2	0.01561 (11)	0.20180 (13)	−0.04931 (10)	0.0629 (4)
H2	0.0461	0.2149	−0.0960	0.094*
O3	−0.20731 (11)	0.03822 (11)	0.10448 (9)	0.0555 (4)
N1	−0.01360 (13)	0.10594 (12)	0.11865 (10)	0.0445 (4)
H1A	0.0346	0.1442	0.0910	0.053*
N2	0.03470 (14)	0.05414 (12)	0.21453 (11)	0.0444 (4)
C1	0.21322 (16)	0.29390 (14)	0.24792 (13)	0.0426 (4)
C2	0.21798 (15)	0.17485 (15)	0.22370 (12)	0.0397 (4)
C3	0.28605 (16)	0.14187 (17)	0.15787 (14)	0.0496 (5)
H3	0.2892	0.0623	0.1412	0.060*
C4	0.34956 (16)	0.22417 (19)	0.11622 (14)	0.0546 (5)
C5	0.34352 (18)	0.34066 (19)	0.14234 (14)	0.0566 (5)
H5	0.3857	0.3972	0.1156	0.068*
C6	0.27685 (18)	0.37622 (17)	0.20703 (14)	0.0553 (5)
H6	0.2744	0.4560	0.2235	0.066*
C7	0.4215 (2)	0.1856 (2)	0.04319 (17)	0.0788 (7)
H7A	0.4735	0.2495	0.0337	0.118*
H7B	0.3640	0.1644	−0.0216	0.118*
H7C	0.4725	0.1184	0.0713	0.118*
C8	0.14484 (16)	0.08723 (14)	0.26466 (13)	0.0416 (4)
C9	0.20075 (18)	0.03997 (16)	0.37216 (14)	0.0538 (5)
H9	0.2179	0.1089	0.4178	0.065*
C10	0.1119 (2)	−0.0383 (2)	0.40763 (17)	0.0856 (8)
H10A	0.0360	0.0042	0.4018	0.128*
H10B	0.1495	−0.0605	0.4777	0.128*
H10C	0.0938	−0.1081	0.3658	0.128*
C11	0.3253 (2)	−0.0202 (2)	0.38364 (17)	0.0832 (7)
H11A	0.3138	−0.0853	0.3366	0.125*
H11B	0.3584	−0.0490	0.4524	0.125*
H11C	0.3824	0.0357	0.3692	0.125*
C12	−0.13535 (15)	0.09610 (14)	0.06947 (13)	0.0399 (4)
C13	−0.18372 (15)	0.16196 (14)	−0.02863 (12)	0.0394 (4)
C14	−0.11049 (17)	0.21255 (15)	−0.08482 (13)	0.0443 (4)
C15	−0.1663 (2)	0.27366 (17)	−0.17470 (15)	0.0580 (5)
H15	−0.1175	0.3059	−0.2125	0.070*
C16	−0.2935 (2)	0.28657 (18)	−0.20782 (16)	0.0655 (6)
H16	−0.3301	0.3283	−0.2678	0.079*
C17	−0.3677 (2)	0.23870 (19)	−0.15361 (16)	0.0633 (6)
H17	−0.4538	0.2483	−0.1762	0.076*
C18	−0.31253 (17)	0.17651 (16)	−0.06546 (15)	0.0522 (5)
H18	−0.3627	0.1431	−0.0293	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0832 (10)	0.0437 (7)	0.0734 (9)	0.0020 (7)	0.0506 (8)	−0.0056 (7)
O2	0.0526 (8)	0.0929 (11)	0.0496 (8)	−0.0065 (7)	0.0248 (7)	0.0118 (7)
O3	0.0500 (8)	0.0617 (8)	0.0590 (8)	−0.0089 (6)	0.0224 (7)	0.0137 (6)
N1	0.0446 (8)	0.0515 (9)	0.0388 (8)	−0.0079 (6)	0.0144 (7)	0.0083 (7)
N2	0.0531 (9)	0.0425 (8)	0.0390 (8)	−0.0005 (7)	0.0159 (7)	0.0044 (6)
C1	0.0462 (10)	0.0433 (10)	0.0424 (10)	0.0036 (8)	0.0193 (8)	−0.0023 (8)
C2	0.0377 (9)	0.0448 (10)	0.0356 (9)	0.0011 (7)	0.0091 (7)	−0.0026 (7)
C3	0.0451 (10)	0.0563 (11)	0.0489 (11)	−0.0003 (8)	0.0159 (9)	−0.0156 (9)
C4	0.0395 (10)	0.0822 (15)	0.0439 (11)	−0.0058 (9)	0.0150 (9)	−0.0101 (10)
C5	0.0545 (12)	0.0673 (13)	0.0523 (12)	−0.0135 (10)	0.0222 (10)	0.0019 (10)
C6	0.0665 (13)	0.0441 (10)	0.0600 (12)	−0.0056 (9)	0.0258 (10)	−0.0020 (9)
C7	0.0599 (13)	0.119 (2)	0.0680 (15)	−0.0099 (12)	0.0356 (12)	−0.0210 (13)
C8	0.0488 (10)	0.0365 (9)	0.0405 (10)	0.0040 (8)	0.0145 (8)	−0.0015 (8)
C9	0.0671 (13)	0.0478 (11)	0.0421 (11)	0.0050 (9)	0.0090 (9)	0.0029 (8)
C10	0.103 (2)	0.0882 (18)	0.0617 (14)	−0.0075 (14)	0.0178 (14)	0.0322 (13)
C11	0.0838 (17)	0.0863 (17)	0.0682 (15)	0.0305 (13)	0.0047 (13)	0.0085 (13)
C12	0.0441 (10)	0.0372 (9)	0.0424 (10)	−0.0035 (7)	0.0189 (8)	−0.0023 (7)
C13	0.0462 (10)	0.0373 (9)	0.0374 (9)	−0.0018 (7)	0.0161 (8)	−0.0043 (7)
C14	0.0482 (10)	0.0467 (10)	0.0395 (10)	−0.0063 (8)	0.0154 (8)	−0.0023 (8)
C15	0.0756 (15)	0.0597 (12)	0.0397 (11)	−0.0133 (10)	0.0185 (10)	0.0026 (9)
C16	0.0818 (16)	0.0580 (13)	0.0460 (12)	−0.0033 (11)	0.0021 (11)	0.0042 (9)
C17	0.0544 (12)	0.0653 (13)	0.0603 (13)	0.0054 (10)	0.0012 (10)	−0.0001 (11)
C18	0.0468 (11)	0.0572 (11)	0.0542 (12)	−0.0003 (9)	0.0172 (9)	−0.0044 (10)

Geometric parameters (Å, º) top

O1—C1	1.3615 (19)	C7—H7C	0.9600
O1—H1	0.8200	C8—C9	1.515 (2)
O2—C14	1.360 (2)	C9—C10	1.513 (3)
O2—H2	0.8200	C9—C11	1.519 (3)
O3—C12	1.2377 (19)	C9—H9	0.9800
N1—C12	1.338 (2)	C10—H10A	0.9600
N1—N2	1.3909 (19)	C10—H10B	0.9600
N1—H1A	0.8600	C10—H10C	0.9600
N2—C8	1.280 (2)	C11—H11A	0.9600
C1—C6	1.385 (2)	C11—H11B	0.9600
C1—C2	1.389 (2)	C11—H11C	0.9600
C2—C3	1.389 (2)	C12—C13	1.489 (2)
C2—C8	1.494 (2)	C13—C18	1.393 (2)
C3—C4	1.389 (3)	C13—C14	1.399 (2)
C3—H3	0.9300	C14—C15	1.387 (3)
C4—C5	1.369 (3)	C15—C16	1.372 (3)
C4—C7	1.518 (2)	C15—H15	0.9300
C5—C6	1.373 (3)	C16—C17	1.376 (3)
C5—H5	0.9300	C16—H16	0.9300
C6—H6	0.9300	C17—C18	1.374 (3)
C7—H7A	0.9600	C17—H17	0.9300
C7—H7B	0.9600	C18—H18	0.9300

C1—O1—H1	109.5	C10—C9—H9	106.6
C14—O2—H2	109.5	C8—C9—H9	106.6
C12—N1—N2	119.78 (13)	C11—C9—H9	106.6
C12—N1—H1A	120.1	C9—C10—H10A	109.5
N2—N1—H1A	120.1	C9—C10—H10B	109.5
C8—N2—N1	115.46 (14)	H10A—C10—H10B	109.5
O1—C1—C6	122.51 (15)	C9—C10—H10C	109.5
O1—C1—C2	117.92 (15)	H10A—C10—H10C	109.5
C6—C1—C2	119.56 (16)	H10B—C10—H10C	109.5
C1—C2—C3	118.68 (16)	C9—C11—H11A	109.5
C1—C2—C8	119.21 (14)	C9—C11—H11B	109.5
C3—C2—C8	122.03 (15)	H11A—C11—H11B	109.5
C2—C3—C4	122.00 (18)	C9—C11—H11C	109.5
C2—C3—H3	119.0	H11A—C11—H11C	109.5
C4—C3—H3	119.0	H11B—C11—H11C	109.5
C5—C4—C3	117.72 (16)	O3—C12—N1	122.33 (15)
C5—C4—C7	121.53 (18)	O3—C12—C13	120.26 (15)
C3—C4—C7	120.74 (19)	N1—C12—C13	117.38 (13)
C4—C5—C6	121.73 (17)	C18—C13—C14	117.82 (16)
C4—C5—H5	119.1	C18—C13—C12	116.76 (14)
C6—C5—H5	119.1	C14—C13—C12	125.40 (15)
C5—C6—C1	120.31 (18)	O2—C14—C15	120.87 (16)
C5—C6—H6	119.8	O2—C14—C13	118.95 (15)
C1—C6—H6	119.8	C15—C14—C13	120.18 (17)
C4—C7—H7A	109.5	C16—C15—C14	120.07 (18)
C4—C7—H7B	109.5	C16—C15—H15	120.0
H7A—C7—H7B	109.5	C14—C15—H15	120.0
C4—C7—H7C	109.5	C15—C16—C17	121.00 (19)
H7A—C7—H7C	109.5	C15—C16—H16	119.5
H7B—C7—H7C	109.5	C17—C16—H16	119.5
N2—C8—C2	122.85 (15)	C18—C17—C16	118.89 (19)
N2—C8—C9	118.46 (15)	C18—C17—H17	120.6
C2—C8—C9	118.62 (15)	C16—C17—H17	120.6
C10—C9—C8	113.01 (17)	C17—C18—C13	122.03 (18)
C10—C9—C11	112.20 (18)	C17—C18—H18	119.0
C8—C9—C11	111.40 (16)	C13—C18—H18	119.0

C12—N1—N2—C8	−166.53 (15)	C2—C8—C9—C10	174.27 (17)
O1—C1—C2—C3	178.11 (16)	N2—C8—C9—C11	124.62 (19)
C6—C1—C2—C3	−0.6 (3)	C2—C8—C9—C11	−58.3 (2)
O1—C1—C2—C8	1.2 (2)	N2—N1—C12—O3	−2.8 (2)
C6—C1—C2—C8	−177.50 (16)	N2—N1—C12—C13	174.85 (14)
C1—C2—C3—C4	0.3 (3)	O3—C12—C13—C18	13.7 (2)
C8—C2—C3—C4	177.10 (16)	N1—C12—C13—C18	−163.97 (15)
C2—C3—C4—C5	0.2 (3)	O3—C12—C13—C14	−168.03 (16)
C2—C3—C4—C7	−179.04 (17)	N1—C12—C13—C14	14.3 (2)
C3—C4—C5—C6	−0.3 (3)	C18—C13—C14—O2	178.59 (16)
C7—C4—C5—C6	178.90 (19)	C12—C13—C14—O2	0.4 (2)
C4—C5—C6—C1	0.0 (3)	C18—C13—C14—C15	−0.7 (2)
O1—C1—C6—C5	−178.17 (18)	C12—C13—C14—C15	−178.97 (16)
C2—C1—C6—C5	0.5 (3)	O2—C14—C15—C16	−178.11 (17)
N1—N2—C8—C2	−0.4 (2)	C13—C14—C15—C16	1.2 (3)
N1—N2—C8—C9	176.55 (14)	C14—C15—C16—C17	−0.6 (3)
C1—C2—C8—N2	93.6 (2)	C15—C16—C17—C18	−0.5 (3)
C3—C2—C8—N2	−83.1 (2)	C16—C17—C18—C13	0.9 (3)
C1—C2—C8—C9	−83.3 (2)	C14—C13—C18—C17	−0.3 (3)
C3—C2—C8—C9	99.94 (19)	C12—C13—C18—C17	178.06 (17)
N2—C8—C9—C10	−2.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.86	1.98	2.6413 (18)	133
O2—H2···O1ⁱ	0.82	1.96	2.7249 (17)	155
O1—H1···O3ⁱⁱ	0.82	1.90	2.6787 (18)	158

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀N₂O₃
M_r	312.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	11.2144 (11), 11.2887 (11), 13.6535 (13)
β (°)	107.000 (2)
V (Å³)	1653.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.22 × 0.16

Data collection
Diffractometer	Bruker APEX2 CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.987, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	8523, 2924, 2094
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.139, 1.00
No. of reflections	2924
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.15

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.86	1.98	2.6413 (18)	133.4
O2—H2···O1ⁱ	0.82	1.96	2.7249 (17)	154.6
O1—H1···O3ⁱⁱ	0.82	1.90	2.6787 (18)	157.9

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, y+1/2, −z+1/2.

Acknowledgements

This project was supported by the Postgraduate Foundation of Taishan University (No. Y05–2–09).

References

Bruker (2005). APEX2 (Version 1.27) and SAINT (Version 7.12). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Carcelli, M., Mazza, P., Pelizzi, G. & Zani, F. (1995). J. Inorg. Biochem. 57, 43–62. CrossRef CAS PubMed Web of Science Google Scholar
Salem, A. A. (1998). Microchem. J. 60, 51–66. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997b). SHELXTL. Version 5.10. Bruker AXS Inc.,Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2003). SADABS. Version 2.10. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-Hydr­­oxy-N′-[(1Z)-1-(2-hydr­­oxy-5-methyl­phen­yl)-2-methyl­propyl­­idene]benzohydrazide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-Hydroxy-N′-[(1Z)-1-(2-hydroxy-5-methylphenyl)-2-methylpropylidene]benzohydrazide