The cocrystal 2-hydr­oxy-4-methyl-N-propanoylbenzohydrazide–2-hydr­oxy-N-(2-hydr­oxy-4-methyl­benzo­yl)-6-methyl­benzohydrazide (2/1)

Feng, H.-M.; Wang, X.; Lei, K.-W.

doi:10.1107/S1600536808033515

organic compounds

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Volume 64| Part 11| November 2008| Page o2144

doi:10.1107/S1600536808033515

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The cocrystal 2-hydroxy-4-methyl-N-propanoylbenzohydrazide–2-hydroxy-N-(2-hydroxy-4-methylbenzoyl)-6-methylbenzohydrazide (2/1)

Hai-Mei Feng,^a Xin Wang ^b and Ke-Wei Lei ^a ^*

^aState Key Laboratory Base of Novel Functional Materials and Preparation Science, Institute of Solid Materials Chemistry, Faculty of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, People's Republic of China, and ^bZhejiang Textile and Fashion College, Ningbo 315211, People's Republic of China
^*Correspondence e-mail: leikeweipublic@hotmail.com

(Received 16 September 2008; accepted 15 October 2008; online 18 October 2008)

The asymmetric unit of the title compound, 2C₁₁H₁₄N₂O₃·C₁₆H₁₆N₂O₄, contains one molecule of 2-hydroxy-4-methyl-N-propanoylbenzohydrazide and one-half of a molecule of 2-hydroxy-N-(2-hydroxy-4-methylbenzoyl)-6-methylbenzohydrazide. The latter is located on a centre of inversion. Intramolecular N—H⋯O interactions stabilize the conformations of both molecules. The crystal structure is stabilized by intermolecular N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For related literature, see: John et al. (2007 ); Majumder et al. (2006 ).

Experimental

Crystal data

2C₁₁H₁₄N₂O₃·C₁₆H₁₆N₂O₄
M_r = 744.79
Triclinic, $[P \overline 1]$
a = 6.5778 (10) Å
b = 10.7618 (17) Å
c = 13.936 (2) Å
α = 109.522 (3)°
β = 93.608 (1)°
γ = 104.448 (4)°
V = 888.8 (2) Å³
Z = 1
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 (2) K
0.54 × 0.30 × 0.25 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.964, T_max = 0.975
5076 measured reflections
4125 independent reflections
1865 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.110
S = 0.90
4125 reflections
246 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1D⋯O1	0.86	1.93	2.620 (2)	136
O1—H1E⋯O4	0.82	1.87	2.682 (2)	169
N2—H2A⋯O2ⁱ	0.86	2.03	2.866 (2)	165
N3—H3B⋯O5	0.84 (2)	1.94 (3)	2.613 (3)	136 (2)
N3—H3B⋯O4ⁱⁱ	0.84 (2)	2.37 (3)	2.655 (3)	101 (2)
O5—H5B⋯O3ⁱⁱ	0.89 (3)	1.80 (3)	2.685 (2)	175 (2)
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+2, -y+1, -z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808033515/bt2793sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808033515/bt2793Isup2.hkl

checkCIF report

Comment top

N-Acylsalicylhydrazides are an interesting class of compounds because of their unique properties. They have been used extensively as ligands in coordination chemistry. N-acylsalicylhydrazide compounds show photoluminescence in the solid state by proton transfer from O atom to the imine N atom (Majumder et al., 2006). The nuclearity and the shape of the metallamacrocycles could be modulated by controlling the steric interactions caused by N-acyl tails of the ligands (John et al., 2007).

A view of the title structure is illustrated in Fig. 1. The asymmetric unit contains one molecule of 2-hydroxy-4-methyl-N-propanoylbenzohydrazide and half a molecule of 2-hydroxy-N-(2-hydroxy-4-methylbenzoyl)-6-methylbenzohydrazide.

The molecular conformation is characterized by N—H···O hydrogen bonds and the crystal packing is stabilized by N—H···O and O—H···O hydrogen bonds (Fig. 2).

Related literature top

For related literature, see: John et al. (2007); Majumder et al. (2006). [Please provide details of recrystallisation solvent to complete the sentence "The filtrate was evaporated using a rotary evaporator and recrystallized from" in the Experimental section]

Experimental top

Propionic anhydride (0.26 g, 2.00 mmol) and 2-hydroxy-4-methylbenzohydrazide (0.31 g, 1.80 mmol) were stirred with an external ice-water bath in DMF (20 ml) for 6 h. The filtrate was evaporated on a rotary evaporator. After recrystallization, the title compound were obtained.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SMART (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme [symmetry code: (A) -x + 2, -y + 1, -z].
	Fig. 2. Packing diagram of the title compound.

2-hydroxy-4-methyl-N-propanoylbenzohydrazide– 2-hydroxy-N-(2-hydroxy-4-methylbenzoyl)-6-methylbenzohydrazide (2/1) top

Crystal data top

2C₁₁H₁₄N₂O₃·C₁₆H₁₆N₂O₄	Z = 1
M_r = 744.79	F(000) = 394
Triclinic, P1	D_x = 1.391 Mg m⁻³
Hall symbol: -P 1	Melting point = 488–496 K
a = 6.5778 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.7618 (17) Å	Cell parameters from 6530 reflections
c = 13.936 (2) Å	θ = 1.0–27.6°
α = 109.522 (3)°	µ = 0.10 mm⁻¹
β = 93.608 (1)°	T = 296 K
γ = 104.448 (4)°	Block, colourless
V = 888.8 (2) Å³	0.54 × 0.30 × 0.25 mm

Data collection top

Bruker APEXII diffractometer	4125 independent reflections
Radiation source: fine-focus sealed tube	1865 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 0 pixels mm^-1	θ_max = 27.6°, θ_min = 1.0°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −14→14
T_min = 0.964, T_max = 0.975	l = −18→18
5076 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 0.90	w = 1/[σ²(F_o²) + (0.0665P)² + 0.5716P] where P = (F_o² + 2F_c²)/3
4125 reflections	(Δ/σ)_max = 0.001
246 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

2C₁₁H₁₄N₂O₃·C₁₆H₁₆N₂O₄	γ = 104.448 (4)°
M_r = 744.79	V = 888.8 (2) Å³
Triclinic, P1	Z = 1
a = 6.5778 (10) Å	Mo Kα radiation
b = 10.7618 (17) Å	µ = 0.10 mm⁻¹
c = 13.936 (2) Å	T = 296 K
α = 109.522 (3)°	0.54 × 0.30 × 0.25 mm
β = 93.608 (1)°

Data collection top

Bruker APEXII diffractometer	4125 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1865 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.975	R_int = 0.022
5076 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 0.90	Δρ_max = 0.20 e Å⁻³
4125 reflections	Δρ_min = −0.22 e Å⁻³
246 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 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.

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

	x	y	z	U_iso*/U_eq
C1	1.5753 (4)	1.1759 (2)	0.25135 (19)	0.0371 (6)
H1A	1.6241	1.2745	0.2819	0.056*
H1B	1.5448	1.1483	0.1777	0.056*
H1C	1.6836	1.1382	0.2689	0.056*
C2	1.3767 (3)	1.1237 (2)	0.29126 (16)	0.0272 (5)
C3	1.2717 (3)	1.2119 (2)	0.35009 (16)	0.0302 (5)
H3A	1.3247	1.3062	0.3659	0.036*
C4	1.0896 (3)	1.1610 (2)	0.38542 (16)	0.0272 (5)
H4A	1.0227	1.2222	0.4251	0.033*
C5	1.2941 (3)	0.9840 (2)	0.27002 (16)	0.0271 (5)
H5A	1.3639	0.9236	0.2317	0.032*
C6	1.1100 (3)	0.9315 (2)	0.30440 (15)	0.0243 (5)
C7	1.0027 (3)	1.0199 (2)	0.36312 (15)	0.0230 (5)
C8	0.8034 (3)	0.9769 (2)	0.40407 (15)	0.0230 (5)
C9	0.4670 (3)	0.6593 (2)	0.40029 (15)	0.0272 (5)
C10	0.2783 (3)	0.6153 (2)	0.44886 (17)	0.0356 (6)
H10A	0.2494	0.6963	0.4956	0.043*
H10B	0.3117	0.5625	0.4890	0.043*
C11	0.0800 (4)	0.5283 (3)	0.3690 (2)	0.0434 (6)
H11A	−0.0362	0.5022	0.4034	0.065*
H11B	0.1071	0.4472	0.3232	0.065*
H11C	0.0442	0.5809	0.3303	0.065*
C12	2.0539 (4)	0.8165 (3)	−0.0799 (2)	0.0423 (6)
H12A	2.0282	0.8592	−0.1281	0.063*
H12B	2.1120	0.7422	−0.1122	0.063*
H12C	2.1528	0.8831	−0.0208	0.063*
C13	1.8475 (3)	0.7613 (2)	−0.04652 (17)	0.0312 (5)
C14	1.8192 (3)	0.8096 (2)	0.05601 (17)	0.0331 (5)
H14A	1.9293	0.8769	0.1054	0.040*
C15	1.6810 (3)	0.6616 (2)	−0.11824 (16)	0.0293 (5)
H15A	1.6985	0.6282	−0.1870	0.035*
C16	1.4884 (3)	0.6101 (2)	−0.08999 (16)	0.0267 (5)
C17	1.6287 (3)	0.7582 (2)	0.08499 (17)	0.0320 (5)
H17A	1.6136	0.7910	0.1541	0.038*
C18	1.4587 (3)	0.6587 (2)	0.01368 (16)	0.0257 (5)
C19	1.2600 (3)	0.6131 (2)	0.05327 (16)	0.0252 (5)
N1	0.7128 (3)	0.84114 (17)	0.37670 (13)	0.0273 (4)
H1D	0.7663	0.7838	0.3347	0.033*
N2	0.5341 (3)	0.79291 (17)	0.41560 (13)	0.0263 (4)
H2A	0.4672	0.8484	0.4492	0.032*
O4	1.2460 (2)	0.65694 (15)	0.14648 (11)	0.0333 (4)
O1	1.0312 (2)	0.79309 (14)	0.28105 (11)	0.0322 (4)
H1E	1.1084	0.7533	0.2467	0.048*
O2	0.7227 (2)	1.06102 (14)	0.45964 (11)	0.0314 (4)
O3	0.5567 (2)	0.57635 (14)	0.34881 (11)	0.0329 (4)
N3	1.0943 (3)	0.52334 (18)	−0.01587 (15)	0.0291 (5)
O5	1.3246 (2)	0.51267 (15)	−0.16289 (12)	0.0333 (4)
H3B	1.104 (4)	0.490 (2)	−0.0786 (19)	0.036 (7)*
H5B	1.368 (4)	0.481 (3)	−0.223 (2)	0.055 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0265 (12)	0.0416 (14)	0.0485 (14)	0.0077 (11)	0.0136 (10)	0.0233 (11)
C2	0.0192 (11)	0.0345 (13)	0.0299 (12)	0.0067 (10)	0.0031 (9)	0.0148 (10)
C3	0.0249 (12)	0.0268 (12)	0.0401 (13)	0.0045 (10)	0.0048 (10)	0.0158 (10)
C4	0.0249 (12)	0.0262 (12)	0.0316 (12)	0.0094 (10)	0.0067 (9)	0.0100 (9)
C5	0.0226 (12)	0.0307 (12)	0.0293 (12)	0.0108 (10)	0.0085 (9)	0.0096 (9)
C6	0.0235 (12)	0.0234 (12)	0.0256 (11)	0.0058 (9)	0.0056 (9)	0.0089 (9)
C7	0.0196 (11)	0.0280 (12)	0.0221 (11)	0.0073 (9)	0.0038 (8)	0.0095 (9)
C8	0.0208 (11)	0.0267 (12)	0.0222 (11)	0.0079 (10)	0.0042 (9)	0.0087 (9)
C9	0.0287 (12)	0.0254 (12)	0.0253 (11)	0.0071 (10)	0.0090 (9)	0.0060 (9)
C10	0.0349 (13)	0.0255 (12)	0.0442 (14)	0.0059 (10)	0.0223 (11)	0.0088 (10)
C11	0.0267 (13)	0.0530 (15)	0.0628 (17)	0.0105 (12)	0.0157 (12)	0.0356 (13)
C12	0.0302 (13)	0.0454 (14)	0.0524 (15)	0.0062 (11)	0.0121 (11)	0.0216 (12)
C13	0.0278 (12)	0.0308 (12)	0.0407 (14)	0.0104 (10)	0.0087 (10)	0.0182 (11)
C14	0.0267 (13)	0.0323 (13)	0.0373 (13)	0.0046 (10)	0.0022 (10)	0.0122 (10)
C15	0.0303 (13)	0.0303 (12)	0.0302 (12)	0.0104 (10)	0.0108 (10)	0.0123 (10)
C16	0.0259 (12)	0.0248 (11)	0.0302 (12)	0.0090 (9)	0.0061 (9)	0.0093 (9)
C17	0.0333 (13)	0.0346 (13)	0.0283 (12)	0.0126 (11)	0.0076 (10)	0.0091 (10)
C18	0.0276 (12)	0.0233 (11)	0.0313 (12)	0.0117 (9)	0.0119 (10)	0.0120 (9)
C19	0.0287 (13)	0.0233 (11)	0.0303 (13)	0.0143 (10)	0.0126 (10)	0.0117 (10)
N1	0.0245 (10)	0.0254 (10)	0.0316 (10)	0.0066 (8)	0.0167 (8)	0.0079 (8)
N2	0.0222 (10)	0.0266 (10)	0.0321 (10)	0.0089 (8)	0.0167 (8)	0.0097 (8)
O4	0.0351 (9)	0.0339 (9)	0.0309 (9)	0.0122 (7)	0.0152 (7)	0.0083 (7)
O1	0.0301 (9)	0.0232 (8)	0.0429 (9)	0.0079 (7)	0.0195 (7)	0.0087 (7)
O2	0.0284 (8)	0.0286 (8)	0.0383 (9)	0.0105 (7)	0.0155 (7)	0.0101 (7)
O3	0.0338 (9)	0.0282 (8)	0.0356 (9)	0.0094 (7)	0.0166 (7)	0.0076 (7)
N3	0.0258 (10)	0.0340 (11)	0.0290 (11)	0.0080 (9)	0.0153 (9)	0.0116 (9)
O5	0.0280 (9)	0.0366 (9)	0.0262 (9)	0.0017 (7)	0.0106 (7)	0.0044 (7)

Geometric parameters (Å, º) top

C1—C2	1.505 (3)	C11—H11C	0.9600
C1—H1A	0.9600	C12—C13	1.508 (3)
C1—H1B	0.9600	C12—H12A	0.9600
C1—H1C	0.9600	C12—H12B	0.9600
C2—C5	1.385 (3)	C12—H12C	0.9600
C2—C3	1.388 (3)	C13—C15	1.382 (3)
C3—C4	1.380 (3)	C13—C14	1.390 (3)
C3—H3A	0.9300	C14—C17	1.381 (3)
C4—C7	1.399 (3)	C14—H14A	0.9300
C4—H4A	0.9300	C15—C16	1.387 (3)
C5—C6	1.388 (3)	C15—H15A	0.9300
C5—H5A	0.9300	C16—O5	1.371 (2)
C6—O1	1.365 (2)	C16—C18	1.407 (3)
C6—C7	1.400 (3)	C17—C18	1.391 (3)
C7—C8	1.492 (3)	C17—H17A	0.9300
C8—O2	1.234 (2)	C18—C19	1.485 (3)
C8—N1	1.342 (3)	C19—O4	1.243 (2)
C9—O3	1.244 (2)	C19—N3	1.330 (3)
C9—N2	1.332 (3)	N1—N2	1.382 (2)
C9—C10	1.500 (3)	N1—H1D	0.8600
C10—C11	1.526 (3)	N2—H2A	0.8600
C10—H10A	0.9700	O1—H1E	0.8200
C10—H10B	0.9700	N3—N3ⁱ	1.376 (3)
C11—H11A	0.9600	N3—H3B	0.84 (2)
C11—H11B	0.9600	O5—H5B	0.88 (3)

C2—C1—H1A	109.5	H11A—C11—H11C	109.5
C2—C1—H1B	109.5	H11B—C11—H11C	109.5
H1A—C1—H1B	109.5	C13—C12—H12A	109.5
C2—C1—H1C	109.5	C13—C12—H12B	109.5
H1A—C1—H1C	109.5	H12A—C12—H12B	109.5
H1B—C1—H1C	109.5	C13—C12—H12C	109.5
C5—C2—C3	118.03 (19)	H12A—C12—H12C	109.5
C5—C2—C1	120.00 (19)	H12B—C12—H12C	109.5
C3—C2—C1	121.96 (19)	C15—C13—C14	118.5 (2)
C4—C3—C2	120.70 (19)	C15—C13—C12	120.2 (2)
C4—C3—H3A	119.6	C14—C13—C12	121.3 (2)
C2—C3—H3A	119.6	C17—C14—C13	120.4 (2)
C3—C4—C7	121.80 (19)	C17—C14—H14A	119.8
C3—C4—H4A	119.1	C13—C14—H14A	119.8
C7—C4—H4A	119.1	C13—C15—C16	121.5 (2)
C2—C5—C6	121.78 (19)	C13—C15—H15A	119.3
C2—C5—H5A	119.1	C16—C15—H15A	119.3
C6—C5—H5A	119.1	O5—C16—C15	120.35 (18)
O1—C6—C5	120.36 (17)	O5—C16—C18	119.40 (18)
O1—C6—C7	119.25 (17)	C15—C16—C18	120.25 (19)
C5—C6—C7	120.39 (18)	C14—C17—C18	121.9 (2)
C4—C7—C6	117.28 (18)	C14—C17—H17A	119.1
C4—C7—C8	117.01 (18)	C18—C17—H17A	119.1
C6—C7—C8	125.70 (18)	C17—C18—C16	117.49 (19)
O2—C8—N1	120.91 (18)	C17—C18—C19	117.19 (18)
O2—C8—C7	122.27 (18)	C16—C18—C19	125.33 (19)
N1—C8—C7	116.81 (17)	O4—C19—N3	120.78 (19)
O3—C9—N2	121.63 (19)	O4—C19—C18	122.20 (19)
O3—C9—C10	122.19 (18)	N3—C19—C18	117.01 (18)
N2—C9—C10	116.18 (18)	C8—N1—N2	120.37 (16)
C9—C10—C11	112.34 (18)	C8—N1—H1D	119.8
C9—C10—H10A	109.1	N2—N1—H1D	119.8
C11—C10—H10A	109.1	C9—N2—N1	119.05 (16)
C9—C10—H10B	109.1	C9—N2—H2A	120.5
C11—C10—H10B	109.1	N1—N2—H2A	120.5
H10A—C10—H10B	107.9	C6—O1—H1E	109.5
C10—C11—H11A	109.5	C19—N3—N3ⁱ	119.9 (2)
C10—C11—H11B	109.5	C19—N3—H3B	121.4 (16)
H11A—C11—H11B	109.5	N3ⁱ—N3—H3B	118.6 (16)
C10—C11—H11C	109.5	C16—O5—H5B	110.8 (17)

Symmetry code: (i) −x+2, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···O1	0.86	1.93	2.620 (2)	136
O1—H1E···O4	0.82	1.87	2.682 (2)	169
N2—H2A···O2ⁱⁱ	0.86	2.03	2.866 (2)	165
N3—H3B···O5	0.84 (2)	1.94 (3)	2.613 (3)	136 (2)
N3—H3B···O4ⁱ	0.84 (2)	2.37 (3)	2.655 (3)	101 (2)
O5—H5B···O3ⁱ	0.89 (3)	1.80 (3)	2.685 (2)	175 (2)

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

Experimental details

Crystal data
Chemical formula	2C₁₁H₁₄N₂O₃·C₁₆H₁₆N₂O₄
M_r	744.79
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.5778 (10), 10.7618 (17), 13.936 (2)
α, β, γ (°)	109.522 (3), 93.608 (1), 104.448 (4)
V (Å³)	888.8 (2)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.54 × 0.30 × 0.25

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.964, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	5076, 4125, 1865
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.110, 0.90
No. of reflections	4125
No. of parameters	246
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.22

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···O1	0.8600	1.9300	2.620 (2)	136.00
O1—H1E···O4	0.8200	1.8700	2.682 (2)	169.00
N2—H2A···O2ⁱ	0.8600	2.0300	2.866 (2)	165.00
N3—H3B···O5	0.84 (2)	1.94 (3)	2.613 (3)	136 (2)
N3—H3B···O4ⁱⁱ	0.84 (2)	2.37 (3)	2.655 (3)	101 (2)
O5—H5B···O3ⁱⁱ	0.89 (3)	1.80 (3)	2.685 (2)	175 (2)

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

Acknowledgements

This project was supported by the Talent Fund of Ningbo University (grant No. 2006668) and sponsored by the K. C. Wong Magna Fund of Ningbo University.

References

Bruker (2005). SADABS. Bruker AXS Inc. Madison, Wisconsion, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
John, R. P., Moon, D. Y. & Lah, M. S. (2007). Supramol. Chem. 19, 295–308. Web of Science CrossRef CAS Google Scholar
Majumder, A., Goswami, S., Batten, S. R., El Fallah, M. S., Ribas, J. & Mitra, S. (2006). Inorg. Chim. Acta, 359, 2375–2382. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 11| November 2008| Page o2144

doi:10.1107/S1600536808033515

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

The cocrystal 2-hydr­­oxy-4-methyl-N-propanoylbenzohydrazide–2-hydr­­oxy-N-(2-hydr­­oxy-4-methyl­benzo­yl)-6-methyl­benzohydrazide (2/1)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

The cocrystal 2-hydroxy-4-methyl-N-propanoylbenzohydrazide–2-hydroxy-N-(2-hydroxy-4-methylbenzoyl)-6-methylbenzohydrazide (2/1)