N′-(4-Diethyl­amino-2-hy­droxy­benzyl­idene)-4-(dimethyl­amino)­benzo­hydrazide methanol monosolvate

Su, F.; Gu, Z.-G.; Lin, J.

doi:10.1107/S1600536811019957

organic compounds

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Volume 67| Part 7| July 2011| Page o1634

doi:10.1107/S1600536811019957

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N′-(4-Diethylamino-2-hydroxybenzylidene)-4-(dimethylamino)benzohydrazide methanol monosolvate

Fu Su,^a Zheng-Gui Gu ^a and Jun Lin ^a ^*

^aJiangsu Centre of Extraction Separation Engineering Technology, College of Chemistry and Materials Science, Nanjing Normal University, Nanjing 210046, People's Republic of China
^*Correspondence e-mail: douduo2011@163.com

(Received 25 May 2011; accepted 25 May 2011; online 11 June 2011)

The title compound, C₂₀H₂₆N₄O₂·CH₃OH, was prepared by the reaction of 4-diethylamino-2-hydroxybenzaldehyde with 4-(dimethylamino)benzohydrazide. The dihedral angle between the two benzene rings is 13.6 (3)° and an intramolecular O—H⋯N hydrogen bond generates an S(6) ring. In the crystal, the hydrazone and methanol molecules are linked through intermolecular O—H⋯O and N—H⋯O hydrogen bonds, forming chains along a.

Related literature

For the biological properties of hydrazones, see: Ajani et al. (2010 ); Zhang et al. (2010 ); Angelusiu et al. (2010 ). For similar structures, see: Huang & Wu (2010 ); Khaledi et al. (2010 ); Zhou & Yang (2010 ); Ji & Lu (2010 ); Singh & Singh (2010 ); Ahmad et al. (2010 ). For hydrogen-bond motifs, see Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₀H₂₆N₄O₂·CH₄O
M_r = 386.49
Triclinic, $[P \overline 1]$
a = 6.786 (3) Å
b = 11.791 (3) Å
c = 14.252 (2) Å
α = 111.511 (3)°
β = 92.811 (2)°
γ = 96.492 (2)°
V = 1049.1 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.27 × 0.23 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.978, T_max = 0.983
7543 measured reflections
4421 independent reflections
1809 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.070
wR(F²) = 0.189
S = 1.00
4421 reflections
263 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3	0.90 (1)	2.07 (2)	2.936 (4)	160 (3)
O3—H3⋯O2ⁱ	0.82	1.84	2.661 (3)	177
O1—H1⋯N1	0.82	2.02	2.727 (3)	145
Symmetry code: (i) x+1, y, z.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811019957/sj5154sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811019957/sj5154Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811019957/sj5154Isup3.cml

checkCIF report

Comment top

In the last year, much attention has been focused on the biological properties of hydrazone compounds (Ajani et al., 2010; Zhang et al., 2010; Angelusiu et al., 2010). The crystal structures of a number of hydrazone compounds have also been determined (Huang & Wu, 2010; Khaledi et al., 2010; Zhou & Yang, 2010; Ji & Lu, 2010; Singh & Singh, 2010; Ahmad et al., 2010). In this paper, the title new hydrazone compound, Fig. 1, is reported.

The asymmetric unit of the compound contains a hydrazone molecule and a methanol molecule. The dihedral angle between the two benzene rings is 13.6 (3)° and an intramolecular O1—H1···N1 hydrogen bond forms an S(6) ring (Bernstein et al., 1995). In the crystal structure, the hydrazone and methanol molecules are linked through intermolecular O–H···O and N–H···O hydrogen bonds (Table 1), to form 1D chains along a (Fig. 2).

Related literature top

For the biological properties of hydrazones, see: Ajani et al. (2010); Zhang et al. (2010); Angelusiu et al. (2010). For similar structures, see: Huang & Wu (2010); Khaledi et al. (2010); Zhou & Yang (2010); Ji & Lu (2010); Singh & Singh (2010); Ahmad et al. (2010). For hydrogen-bond motifs, see Bernstein et al. (1995).

Experimental top

The reaction of 4-diethylamino-2-hydroxybenzaldehyde (0.193 g, 1 mmol) with 4-(dimethylamino)benzohydrazide (0.179 g, 1 mmol) in 30 ml methanol at room temperature afforded the title compound. Colorless single crystals were formed by gradual evaporation of the solution in air.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids and the atomic numbering. Hydrogen bonds are drawn as dashed lines.
	Fig. 2. Crystal packing of the title compound, viewed down the b axis. Intermolecular interactions are drawn as dashed lines.

N'-(4-Diethylamino-2-hydroxybenzylidene)-4-(dimethylamino)benzohydrazide methanol monosolvate top

Crystal data top

C₂₀H₂₆N₄O₂·CH₄O	Z = 2
M_r = 386.49	F(000) = 416
Triclinic, P1	D_x = 1.224 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.786 (3) Å	Cell parameters from 765 reflections
b = 11.791 (3) Å	θ = 2.6–24.5°
c = 14.252 (2) Å	µ = 0.08 mm⁻¹
α = 111.511 (3)°	T = 298 K
β = 92.811 (2)°	Block, colorless
γ = 96.492 (2)°	0.27 × 0.23 × 0.21 mm
V = 1049.1 (6) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	4421 independent reflections
Radiation source: fine-focus sealed tube	1809 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
ω scans	θ_max = 27.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→8
T_min = 0.978, T_max = 0.983	k = −15→15
7543 measured reflections	l = −15→18

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.189	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0676P)²] where P = (F_o² + 2F_c²)/3
4421 reflections	(Δ/σ)_max < 0.001
263 parameters	Δρ_max = 0.30 e Å⁻³
1 restraint	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₀H₂₆N₄O₂·CH₄O	γ = 96.492 (2)°
M_r = 386.49	V = 1049.1 (6) Å³
Triclinic, P1	Z = 2
a = 6.786 (3) Å	Mo Kα radiation
b = 11.791 (3) Å	µ = 0.08 mm⁻¹
c = 14.252 (2) Å	T = 298 K
α = 111.511 (3)°	0.27 × 0.23 × 0.21 mm
β = 92.811 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4421 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1809 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.983	R_int = 0.045
7543 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	1 restraint
wR(F²) = 0.189	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.30 e Å⁻³
4421 reflections	Δρ_min = −0.21 e Å⁻³
263 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O1	−0.1048 (3)	0.5092 (2)	0.2045 (2)	0.0741 (8)
H1	−0.0686	0.4564	0.2235	0.111*
O2	−0.0566 (3)	0.2247 (2)	0.3184 (2)	0.0770 (8)
O3	0.6751 (4)	0.3787 (2)	0.3427 (2)	0.0907 (9)
H3	0.7586	0.3321	0.3371	0.136*
N1	0.1680 (4)	0.3808 (2)	0.2520 (2)	0.0549 (7)
N2	0.2452 (4)	0.2985 (2)	0.2885 (2)	0.0564 (8)
N3	0.4202 (4)	−0.1790 (2)	0.3829 (2)	0.0632 (8)
N4	0.1131 (4)	0.7762 (2)	0.0366 (2)	0.0705 (9)
C1	0.2398 (4)	0.5230 (2)	0.1692 (2)	0.0488 (8)
C2	0.0478 (5)	0.5553 (3)	0.1644 (2)	0.0487 (8)
C3	0.0066 (4)	0.6387 (3)	0.1211 (2)	0.0535 (9)
H3A	−0.1218	0.6588	0.1194	0.064*
C4	0.1541 (5)	0.6933 (3)	0.0801 (2)	0.0525 (8)
C5	0.3450 (5)	0.6589 (3)	0.0828 (3)	0.0649 (10)
H5	0.4457	0.6922	0.0546	0.078*
C6	0.3848 (5)	0.5769 (3)	0.1263 (3)	0.0594 (9)
H6	0.5130	0.5564	0.1273	0.071*
C7	0.2927 (5)	0.4383 (3)	0.2145 (2)	0.0523 (8)
H7	0.4248	0.4246	0.2168	0.063*
C8	0.1245 (5)	0.2195 (3)	0.3155 (2)	0.0522 (8)
C9	0.2154 (4)	0.1219 (3)	0.3371 (2)	0.0470 (8)
C10	0.0978 (5)	0.0474 (3)	0.3749 (3)	0.0573 (9)
H10	−0.0301	0.0644	0.3897	0.069*
C11	0.1637 (5)	−0.0504 (3)	0.3910 (2)	0.0596 (9)
H11	0.0806	−0.0973	0.4173	0.071*
C12	0.3538 (5)	−0.0806 (3)	0.3687 (2)	0.0505 (8)
C13	0.4723 (4)	−0.0056 (3)	0.3301 (2)	0.0575 (9)
H13	0.6001	−0.0224	0.3148	0.069*
C14	0.4036 (5)	0.0927 (3)	0.3145 (2)	0.0553 (9)
H14	0.4855	0.1402	0.2883	0.066*
C15	0.2976 (6)	−0.2536 (3)	0.4256 (3)	0.0780 (11)
H15A	0.2808	−0.2051	0.4946	0.117*
H15B	0.3614	−0.3231	0.4233	0.117*
H15C	0.1696	−0.2821	0.3869	0.117*
C16	0.6191 (5)	−0.2071 (3)	0.3638 (3)	0.0789 (12)
H16A	0.6412	−0.2160	0.2956	0.118*
H16B	0.6347	−0.2824	0.3728	0.118*
H16C	0.7139	−0.1414	0.4103	0.118*
C17	0.2791 (6)	0.8609 (3)	0.0203 (3)	0.0792 (12)
H17A	0.2346	0.9396	0.0307	0.095*
H17B	0.3917	0.8751	0.0698	0.095*
C18	0.3427 (6)	0.8094 (4)	−0.0821 (3)	0.1027 (14)
H18A	0.3853	0.7310	−0.0929	0.154*
H18B	0.4511	0.8645	−0.0893	0.154*
H18C	0.2332	0.7989	−0.1312	0.154*
C19	−0.0856 (5)	0.8062 (3)	0.0254 (3)	0.0603 (9)
H19A	−0.1818	0.7332	0.0115	0.072*
H19B	−0.0975	0.8310	−0.0322	0.072*
C20	−0.1341 (6)	0.9075 (3)	0.1181 (3)	0.0841 (12)
H20A	−0.1327	0.8810	0.1742	0.126*
H20B	−0.2638	0.9272	0.1057	0.126*
H20C	−0.0366	0.9791	0.1336	0.126*
C21	0.7364 (6)	0.4885 (4)	0.4255 (3)	0.0977 (14)
H21A	0.8506	0.5328	0.4108	0.146*
H21B	0.7706	0.4704	0.4841	0.146*
H21C	0.6301	0.5378	0.4384	0.146*
H2	0.3791 (16)	0.309 (3)	0.290 (3)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0555 (14)	0.0899 (18)	0.111 (2)	0.0186 (12)	0.0232 (14)	0.0730 (17)
O2	0.0539 (15)	0.0793 (16)	0.118 (2)	0.0240 (13)	0.0139 (14)	0.0555 (15)
O3	0.0596 (17)	0.0795 (18)	0.137 (3)	0.0214 (13)	−0.0033 (17)	0.0440 (18)
N1	0.0575 (18)	0.0537 (15)	0.062 (2)	0.0165 (13)	−0.0006 (15)	0.0301 (15)
N2	0.0473 (16)	0.0592 (16)	0.078 (2)	0.0149 (14)	0.0037 (16)	0.0420 (16)
N3	0.071 (2)	0.0561 (16)	0.077 (2)	0.0165 (15)	0.0121 (16)	0.0391 (16)
N4	0.0546 (18)	0.0831 (19)	0.108 (3)	0.0214 (15)	0.0239 (17)	0.070 (2)
C1	0.0493 (19)	0.0476 (17)	0.055 (2)	0.0121 (15)	0.0030 (16)	0.0239 (16)
C2	0.048 (2)	0.0527 (18)	0.051 (2)	0.0079 (15)	0.0085 (16)	0.0261 (17)
C3	0.0428 (19)	0.0593 (19)	0.071 (3)	0.0145 (16)	0.0099 (17)	0.0364 (18)
C4	0.050 (2)	0.0564 (18)	0.062 (2)	0.0109 (16)	0.0111 (17)	0.0329 (18)
C5	0.049 (2)	0.078 (2)	0.091 (3)	0.0170 (18)	0.0227 (19)	0.054 (2)
C6	0.047 (2)	0.064 (2)	0.078 (3)	0.0168 (16)	0.0093 (18)	0.036 (2)
C7	0.051 (2)	0.0497 (18)	0.058 (2)	0.0168 (16)	0.0002 (17)	0.0206 (17)
C8	0.046 (2)	0.0579 (19)	0.058 (2)	0.0172 (16)	0.0043 (17)	0.0248 (17)
C9	0.0447 (19)	0.0527 (18)	0.049 (2)	0.0133 (15)	0.0031 (16)	0.0233 (16)
C10	0.0446 (19)	0.071 (2)	0.070 (3)	0.0175 (16)	0.0158 (17)	0.038 (2)
C11	0.057 (2)	0.066 (2)	0.069 (3)	0.0114 (18)	0.0119 (19)	0.0401 (19)
C12	0.058 (2)	0.0480 (17)	0.050 (2)	0.0094 (16)	−0.0002 (17)	0.0233 (16)
C13	0.0447 (19)	0.061 (2)	0.075 (3)	0.0165 (16)	0.0112 (18)	0.0314 (19)
C14	0.050 (2)	0.0555 (18)	0.072 (3)	0.0133 (16)	0.0117 (18)	0.0353 (18)
C15	0.108 (3)	0.061 (2)	0.079 (3)	0.020 (2)	0.015 (2)	0.040 (2)
C16	0.071 (3)	0.069 (2)	0.109 (3)	0.0221 (19)	0.004 (2)	0.043 (2)
C17	0.079 (3)	0.083 (2)	0.094 (4)	0.025 (2)	0.017 (2)	0.050 (2)
C18	0.113 (4)	0.129 (4)	0.092 (4)	0.038 (3)	0.036 (3)	0.062 (3)
C19	0.058 (2)	0.066 (2)	0.069 (3)	0.0134 (17)	0.0033 (19)	0.038 (2)
C20	0.085 (3)	0.080 (3)	0.089 (3)	0.023 (2)	0.011 (2)	0.030 (2)
C21	0.101 (3)	0.090 (3)	0.114 (4)	0.029 (3)	0.024 (3)	0.046 (3)

Geometric parameters (Å, º) top

O1—C2	1.362 (3)	C10—C11	1.373 (4)
O1—H1	0.8200	C10—H10	0.9300
O2—C8	1.239 (3)	C11—C12	1.397 (4)
O3—C21	1.397 (4)	C11—H11	0.9300
O3—H3	0.8200	C12—C13	1.404 (4)
N1—C7	1.281 (4)	C13—C14	1.383 (4)
N1—N2	1.396 (3)	C13—H13	0.9300
N2—C8	1.344 (4)	C14—H14	0.9300
N2—H2	0.900 (10)	C15—H15A	0.9600
N3—C12	1.368 (3)	C15—H15B	0.9600
N3—C16	1.441 (4)	C15—H15C	0.9600
N3—C15	1.454 (4)	C16—H16A	0.9600
N4—C4	1.381 (4)	C16—H16B	0.9600
N4—C19	1.448 (4)	C16—H16C	0.9600
N4—C17	1.504 (4)	C17—C18	1.469 (5)
C1—C6	1.396 (4)	C17—H17A	0.9700
C1—C2	1.403 (4)	C17—H17B	0.9700
C1—C7	1.441 (4)	C18—H18A	0.9600
C2—C3	1.384 (4)	C18—H18B	0.9600
C3—C4	1.395 (4)	C18—H18C	0.9600
C3—H3A	0.9300	C19—C20	1.501 (5)
C4—C5	1.404 (4)	C19—H19A	0.9700
C5—C6	1.369 (4)	C19—H19B	0.9700
C5—H5	0.9300	C20—H20A	0.9600
C6—H6	0.9300	C20—H20B	0.9600
C7—H7	0.9300	C20—H20C	0.9600
C8—C9	1.484 (4)	C21—H21A	0.9600
C9—C14	1.382 (4)	C21—H21B	0.9600
C9—C10	1.389 (4)	C21—H21C	0.9600

C2—O1—H1	109.5	C14—C13—C12	121.6 (3)
C21—O3—H3	109.5	C14—C13—H13	119.2
C7—N1—N2	115.4 (3)	C12—C13—H13	119.2
C8—N2—N1	121.0 (3)	C9—C14—C13	121.3 (3)
C8—N2—H2	129 (2)	C9—C14—H14	119.4
N1—N2—H2	110 (2)	C13—C14—H14	119.4
C12—N3—C16	121.6 (3)	N3—C15—H15A	109.5
C12—N3—C15	121.0 (3)	N3—C15—H15B	109.5
C16—N3—C15	117.3 (3)	H15A—C15—H15B	109.5
C4—N4—C19	122.5 (3)	N3—C15—H15C	109.5
C4—N4—C17	120.5 (3)	H15A—C15—H15C	109.5
C19—N4—C17	115.6 (2)	H15B—C15—H15C	109.5
C6—C1—C2	116.7 (3)	N3—C16—H16A	109.5
C6—C1—C7	119.4 (3)	N3—C16—H16B	109.5
C2—C1—C7	123.9 (3)	H16A—C16—H16B	109.5
O1—C2—C3	116.9 (3)	N3—C16—H16C	109.5
O1—C2—C1	121.8 (3)	H16A—C16—H16C	109.5
C3—C2—C1	121.3 (3)	H16B—C16—H16C	109.5
C2—C3—C4	121.2 (3)	C18—C17—N4	111.6 (3)
C2—C3—H3A	119.4	C18—C17—H17A	109.3
C4—C3—H3A	119.4	N4—C17—H17A	109.3
N4—C4—C3	121.3 (3)	C18—C17—H17B	109.3
N4—C4—C5	121.2 (3)	N4—C17—H17B	109.3
C3—C4—C5	117.5 (3)	H17A—C17—H17B	108.0
C6—C5—C4	120.9 (3)	C17—C18—H18A	109.5
C6—C5—H5	119.6	C17—C18—H18B	109.5
C4—C5—H5	119.6	H18A—C18—H18B	109.5
C5—C6—C1	122.4 (3)	C17—C18—H18C	109.5
C5—C6—H6	118.8	H18A—C18—H18C	109.5
C1—C6—H6	118.8	H18B—C18—H18C	109.5
N1—C7—C1	123.7 (3)	N4—C19—C20	112.6 (3)
N1—C7—H7	118.2	N4—C19—H19A	109.1
C1—C7—H7	118.2	C20—C19—H19A	109.1
O2—C8—N2	121.6 (3)	N4—C19—H19B	109.1
O2—C8—C9	121.1 (3)	C20—C19—H19B	109.1
N2—C8—C9	117.2 (3)	H19A—C19—H19B	107.8
C14—C9—C10	117.2 (3)	C19—C20—H20A	109.5
C14—C9—C8	124.7 (3)	C19—C20—H20B	109.5
C10—C9—C8	117.9 (3)	H20A—C20—H20B	109.5
C11—C10—C9	122.3 (3)	C19—C20—H20C	109.5
C11—C10—H10	118.8	H20A—C20—H20C	109.5
C9—C10—H10	118.8	H20B—C20—H20C	109.5
C10—C11—C12	121.0 (3)	O3—C21—H21A	109.5
C10—C11—H11	119.5	O3—C21—H21B	109.5
C12—C11—H11	119.5	H21A—C21—H21B	109.5
N3—C12—C11	121.6 (3)	O3—C21—H21C	109.5
N3—C12—C13	121.7 (3)	H21A—C21—H21C	109.5
C11—C12—C13	116.7 (3)	H21B—C21—H21C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3	0.90 (1)	2.07 (2)	2.936 (4)	160 (3)
O3—H3···O2ⁱ	0.82	1.84	2.661 (3)	177
O1—H1···N1	0.82	2.02	2.727 (3)	145

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₆N₄O₂·CH₄O
M_r	386.49
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.786 (3), 11.791 (3), 14.252 (2)
α, β, γ (°)	111.511 (3), 92.811 (2), 96.492 (2)
V (Å³)	1049.1 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.27 × 0.23 × 0.21

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.978, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	7543, 4421, 1809
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.189, 1.00
No. of reflections	4421
No. of parameters	263
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.21

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3	0.900 (10)	2.073 (15)	2.936 (4)	160 (3)
O3—H3···O2ⁱ	0.82	1.84	2.661 (3)	177
O1—H1···N1	0.82	2.02	2.727 (3)	145

Symmetry code: (i) x+1, y, z.

Acknowledgements

We acknowledge the project funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions.

References

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Volume 67| Part 7| July 2011| Page o1634

doi:10.1107/S1600536811019957

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

N′-(4-Di­ethyl­amino-2-hy­dr­oxy­benzyl­­idene)-4-(di­methyl­amino)­benzo­hydrazide methanol monosolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N′-(4-Diethylamino-2-hydroxybenzylidene)-4-(dimethylamino)benzohydrazide methanol monosolvate