1,5-Bis­[1-(2-hy­droxy­phen­yl)ethyl­idene]carbonohydrazide dimethyl­formamide monosolvate

Du, L.; Zhang, W.

doi:10.1107/S1600536810037517

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2645

doi:10.1107/S1600536810037517

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1,5-Bis[1-(2-hydroxyphenyl)ethylidene]carbonohydrazide dimethylformamide monosolvate

Lingyun Du ^a ^* and Wenkang Zhang ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: dulingyun@lcu.edu.cn

(Received 5 September 2010; accepted 19 September 2010; online 30 September 2010)

In the title compound, C₁₇H₁₈N₄O₃·C₃H₇NO, the main disubstituted urea and solvate molecules are linked by pairs of N—H⋯O hydrogen bonds. In the main molecules, the benzene rings form a dihedral angle of 15.59 (13)° a;nd two intramolecular O—H⋯N hydrogen bonds influence the molecular conformation. In the crystal structure, weak intermolecular C—H⋯O interactions link the hydrogen-bonded pairs into chains along the b axis. The chains associate via C—H⋯π interactions.

Related literature

For a related structure, see: Zukerman-Schpector et al. (2009 ). For the bioactivity of carbonohydrazide derivatives, see: Loncle et al. (2004 ); Li et al. (2004 ).

Experimental

Crystal data

C₁₇H₁₈N₄O₃·C₃H₇NO
M_r = 399.45
Monoclinic, P 2₁ /c
a = 16.6372 (15) Å
b = 7.5880 (9) Å
c = 16.2967 (14) Å
β = 94.472 (1)°
V = 2051.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.47 × 0.46 × 0.23 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.958, T_max = 0.979
10277 measured reflections
3596 independent reflections
1712 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.165
S = 1.04
3596 reflections
263 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C12–C17 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4	0.86	2.02	2.805 (3)	151
N3—H3⋯O4	0.86	2.09	2.858 (4)	148
O2—H2A⋯N2	0.82	1.83	2.548 (3)	145
O3—H3A⋯N4	0.82	1.83	2.546 (3)	145
C6—H6⋯O1ⁱ	0.93	2.57	3.241 (4)	129
C10—H10A⋯Cgⁱⁱ	0.96	2.66	3.536 (4)	153
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1.

Data collection: SMART (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 I, global. DOI: 10.1107/S1600536810037517/cv2762sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810037517/cv2762Isup2.hkl

checkCIF report

Comment top

Carbonohydrazide derivatives exhibit various bioactivities such as antibacteriale antifungal, anticonvulsant and anticancer activities (Loncle et al., 2004; Li et al., 2004). Herewith we present the crystal structure of the title compound (I), which is a new carbonohydrazide derivative.

Crystals of (I) comprise equal quantities of a disubstituted urea molecule (M) and a solvent N,N-dimethylformamide molecule (Fig. 1). The bond lengths and angles of the title compound are normal and correspond to those observed in N'',N'''-bis (1-(2-hydroxyphenyl)ethylidene)carbonohydrazide dimethyl sulfoxide solvate (Zukerman-Schpector et al., 2009). The molecular conformation of M is influenced by two intramolecular O—H···N hydrogen bonds (Table 1). Two benzene rings - C4-C9 and C12-C17, respectively - form a dihedral angle of 15.59 (13)°.

In the crystal structure, one M molecule and solvate molecule are paired via N—H···O hydrogen bonds (Table 1). Weak intermolecular C—H···O interactions (Table 1) link hydrogen-bonded pairs into chains along the b axis. The chains associate via C—H···π interactions (Table 1).

Related literature top

For a related structure, see: Zukerman-Schpector et al. (2009). For the bioactivity of carbonohydrazide derivatives, see: Loncle et al. (2004); Li et al. (2004).

Experimental top

2-Hydroxylacetophenone (10.0 mmol) and carbohydrazide (5.0 mmol) were mixed in 50 ml flash After stirring 3 h at 373 K, the resulting mixture was cooled to room temperature, and recrystalized from DMF, and afforded the title compound as a crystalline solid. Elemental analysis: calculated for C₂₀H₂₅N₅O₄: C 60.14, H 6.31, N 17.53%; found: C 60.23, H 6.45, N 17.64%.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (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 content of asymmetric unit of the title compound showing the atomic numbering scheme and 30% probability displacement ellipsoids.

1,5-Bis[1-(2-hydroxyphenyl)ethylidene]carbonohydrazide dimethylformamide monosolvate top

Crystal data top

C₁₇H₁₈N₄O₃·C₃H₇NO	F(000) = 848
M_r = 399.45	D_x = 1.294 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.6372 (15) Å	Cell parameters from 1764 reflections
b = 7.5880 (9) Å	θ = 2.5–21.7°
c = 16.2967 (14) Å	µ = 0.09 mm⁻¹
β = 94.472 (1)°	T = 298 K
V = 2051.1 (4) Å³	Block, colourless
Z = 4	0.47 × 0.46 × 0.23 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3596 independent reflections
Radiation source: fine-focus sealed tube	1712 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
phi and ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→19
T_min = 0.958, T_max = 0.979	k = −9→9
10277 measured reflections	l = −19→19

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.165	w = 1/[σ²(F_o²) + (0.0542P)² + 0.8303P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3596 reflections	Δρ_max = 0.22 e Å⁻³
263 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0049 (10)

Crystal data top

C₁₇H₁₈N₄O₃·C₃H₇NO	V = 2051.1 (4) Å³
M_r = 399.45	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.6372 (15) Å	µ = 0.09 mm⁻¹
b = 7.5880 (9) Å	T = 298 K
c = 16.2967 (14) Å	0.47 × 0.46 × 0.23 mm
β = 94.472 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3596 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1712 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.979	R_int = 0.059
10277 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.165	H-atom parameters constrained
S = 1.04	Δρ_max = 0.22 e Å⁻³
3596 reflections	Δρ_min = −0.17 e Å⁻³
263 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
N1	0.15121 (15)	0.6195 (3)	0.48890 (15)	0.0541 (7)
H1	0.1563	0.6254	0.5417	0.065*
N2	0.08378 (15)	0.6805 (3)	0.44431 (15)	0.0491 (7)
N3	0.27455 (15)	0.4912 (4)	0.49563 (15)	0.0555 (8)
H3	0.2756	0.5015	0.5483	0.067*
N4	0.33674 (15)	0.4171 (3)	0.45841 (15)	0.0510 (7)
N5	0.23936 (17)	0.5436 (4)	0.78637 (16)	0.0602 (8)
O1	0.20609 (13)	0.5357 (3)	0.37093 (14)	0.0717 (8)
O2	0.02424 (14)	0.7754 (4)	0.30242 (13)	0.0772 (8)
H2A	0.0592	0.7362	0.3357	0.116*
O3	0.38946 (14)	0.3282 (4)	0.32185 (14)	0.0826 (8)
H3A	0.3577	0.3729	0.3518	0.124*
O4	0.22303 (16)	0.6047 (4)	0.65032 (15)	0.0825 (9)
C1	0.20997 (19)	0.5488 (4)	0.4450 (2)	0.0511 (9)
C2	0.0191 (2)	0.7253 (5)	0.57328 (18)	0.0606 (10)
H2B	0.0483	0.6243	0.5950	0.091*
H2C	−0.0361	0.7172	0.5863	0.091*
H2D	0.0428	0.8305	0.5973	0.091*
C3	0.02260 (19)	0.7313 (4)	0.48137 (18)	0.0445 (8)
C4	−0.04633 (18)	0.7964 (4)	0.42688 (19)	0.0455 (8)
C5	−0.04176 (19)	0.8178 (4)	0.3417 (2)	0.0516 (9)
C6	−0.1065 (2)	0.8871 (5)	0.2935 (2)	0.0620 (10)
H6	−0.1023	0.9033	0.2374	0.074*
C7	−0.1762 (2)	0.9319 (5)	0.3270 (2)	0.0706 (11)
H7	−0.2193	0.9779	0.2940	0.085*
C8	−0.1824 (2)	0.9086 (5)	0.4098 (3)	0.0792 (12)
H8	−0.2299	0.9381	0.4330	0.095*
C9	−0.1183 (2)	0.8417 (5)	0.4584 (2)	0.0634 (10)
H9	−0.1235	0.8264	0.5143	0.076*
C10	0.40492 (19)	0.3582 (5)	0.59426 (19)	0.0617 (10)
H10A	0.4233	0.4721	0.6132	0.093*
H10B	0.4426	0.2699	0.6148	0.093*
H10C	0.3531	0.3346	0.6139	0.093*
C11	0.39830 (18)	0.3552 (4)	0.50206 (19)	0.0470 (8)
C12	0.46219 (18)	0.2798 (4)	0.4551 (2)	0.0485 (8)
C13	0.4547 (2)	0.2668 (5)	0.3684 (2)	0.0588 (9)
C14	0.5149 (2)	0.1875 (5)	0.3275 (2)	0.0756 (12)
H14	0.5082	0.1747	0.2706	0.091*
C15	0.5839 (2)	0.1277 (5)	0.3690 (3)	0.0799 (12)
H15	0.6244	0.0772	0.3404	0.096*
C16	0.5933 (2)	0.1423 (5)	0.4528 (3)	0.0738 (11)
H16	0.6404	0.1021	0.4813	0.089*
C17	0.5336 (2)	0.2159 (4)	0.4947 (2)	0.0610 (10)
H17	0.5410	0.2237	0.5517	0.073*
C18	0.1982 (2)	0.5477 (5)	0.7144 (2)	0.0700 (11)
H18	0.1458	0.5041	0.7116	0.084*
C19	0.3198 (2)	0.6151 (6)	0.7959 (2)	0.0948 (14)
H19A	0.3380	0.6399	0.7427	0.142*
H19B	0.3553	0.5311	0.8239	0.142*
H19C	0.3195	0.7218	0.8275	0.142*
C20	0.2055 (2)	0.4702 (6)	0.8576 (2)	0.0931 (14)
H20A	0.1503	0.4381	0.8436	0.140*
H20B	0.2080	0.5561	0.9010	0.140*
H20C	0.2356	0.3676	0.8757	0.140*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0494 (16)	0.072 (2)	0.0391 (15)	0.0127 (15)	−0.0055 (13)	−0.0015 (14)
N2	0.0449 (16)	0.0560 (18)	0.0448 (16)	0.0048 (14)	−0.0071 (14)	−0.0012 (13)
N3	0.0466 (16)	0.077 (2)	0.0421 (15)	0.0101 (15)	−0.0048 (13)	−0.0037 (15)
N4	0.0432 (15)	0.0593 (18)	0.0493 (17)	0.0022 (14)	−0.0032 (13)	−0.0033 (14)
N5	0.0661 (19)	0.073 (2)	0.0406 (17)	0.0032 (17)	0.0014 (15)	0.0090 (15)
O1	0.0632 (15)	0.106 (2)	0.0436 (15)	0.0167 (14)	−0.0101 (12)	−0.0117 (14)
O2	0.0669 (16)	0.117 (2)	0.0473 (14)	0.0275 (15)	0.0014 (13)	0.0008 (14)
O3	0.0693 (17)	0.125 (2)	0.0517 (15)	0.0146 (16)	−0.0044 (13)	−0.0063 (15)
O4	0.099 (2)	0.107 (2)	0.0418 (15)	0.0096 (17)	0.0026 (14)	0.0109 (15)
C1	0.0455 (19)	0.058 (2)	0.048 (2)	−0.0022 (17)	−0.0055 (17)	−0.0060 (18)
C2	0.064 (2)	0.068 (2)	0.049 (2)	0.0049 (19)	−0.0020 (17)	0.0008 (18)
C3	0.049 (2)	0.042 (2)	0.0421 (19)	−0.0037 (16)	−0.0026 (16)	−0.0045 (15)
C4	0.0480 (19)	0.0426 (19)	0.045 (2)	0.0011 (16)	−0.0012 (16)	−0.0055 (16)
C5	0.051 (2)	0.058 (2)	0.044 (2)	0.0062 (17)	−0.0033 (17)	−0.0065 (17)
C6	0.067 (2)	0.068 (3)	0.048 (2)	0.007 (2)	−0.0143 (19)	−0.0001 (18)
C7	0.058 (2)	0.081 (3)	0.070 (3)	0.019 (2)	−0.015 (2)	−0.005 (2)
C8	0.053 (2)	0.103 (3)	0.080 (3)	0.022 (2)	0.004 (2)	−0.006 (3)
C9	0.057 (2)	0.078 (3)	0.055 (2)	0.011 (2)	0.0026 (19)	−0.001 (2)
C10	0.061 (2)	0.070 (2)	0.053 (2)	0.0082 (19)	−0.0060 (17)	0.0022 (19)
C11	0.0440 (19)	0.047 (2)	0.049 (2)	−0.0037 (16)	−0.0047 (16)	−0.0020 (16)
C12	0.045 (2)	0.046 (2)	0.054 (2)	−0.0063 (16)	−0.0020 (17)	0.0011 (17)
C13	0.053 (2)	0.065 (2)	0.057 (2)	−0.0051 (19)	−0.0014 (19)	−0.0055 (19)
C14	0.070 (3)	0.093 (3)	0.066 (3)	−0.004 (2)	0.017 (2)	−0.012 (2)
C15	0.068 (3)	0.074 (3)	0.101 (4)	0.006 (2)	0.028 (3)	−0.004 (3)
C16	0.055 (2)	0.072 (3)	0.094 (3)	0.012 (2)	0.004 (2)	0.011 (2)
C17	0.055 (2)	0.058 (2)	0.070 (2)	0.0031 (19)	−0.001 (2)	0.0056 (19)
C18	0.070 (3)	0.075 (3)	0.064 (3)	0.000 (2)	−0.001 (2)	−0.001 (2)
C19	0.072 (3)	0.132 (4)	0.078 (3)	−0.003 (3)	−0.009 (2)	0.010 (3)
C20	0.116 (3)	0.100 (3)	0.066 (3)	0.013 (3)	0.024 (3)	0.025 (2)

Geometric parameters (Å, º) top

N1—C1	1.365 (4)	C7—C8	1.372 (5)
N1—N2	1.369 (3)	C7—H7	0.9300
N1—H1	0.8600	C8—C9	1.375 (5)
N2—C3	1.283 (4)	C8—H8	0.9302
N3—N4	1.361 (3)	C9—H9	0.9300
N3—C1	1.374 (4)	C10—C11	1.498 (4)
N3—H3	0.8600	C10—H10A	0.9600
N4—C11	1.289 (4)	C10—H10B	0.9600
N5—C18	1.311 (4)	C10—H10C	0.9600
N5—C19	1.440 (4)	C11—C12	1.473 (4)
N5—C20	1.441 (4)	C12—C17	1.394 (4)
O1—C1	1.208 (3)	C12—C13	1.411 (4)
O2—C5	1.352 (3)	C13—C14	1.384 (5)
O2—H2A	0.8200	C14—C15	1.364 (5)
O3—C13	1.358 (4)	C14—H14	0.9300
O3—H3A	0.8200	C15—C16	1.367 (5)
O4—C18	1.232 (4)	C15—H15	0.9299
C2—C3	1.504 (4)	C16—C17	1.368 (5)
C2—H2B	0.9600	C16—H16	0.9300
C2—H2C	0.9600	C17—H17	0.9300
C2—H2D	0.9600	C18—H18	0.9300
C3—C4	1.480 (4)	C19—H19A	0.9600
C4—C9	1.382 (4)	C19—H19B	0.9600
C4—C5	1.405 (4)	C19—H19C	0.9600
C5—C6	1.387 (4)	C20—H20A	0.9600
C6—C7	1.363 (5)	C20—H20B	0.9600
C6—H6	0.9300	C20—H20C	0.9600

C1—N1—N2	116.4 (3)	C11—C10—H10A	109.5
C1—N1—H1	121.8	C11—C10—H10B	109.5
N2—N1—H1	121.8	H10A—C10—H10B	109.5
C3—N2—N1	120.0 (3)	C11—C10—H10C	109.5
N4—N3—C1	116.7 (3)	H10A—C10—H10C	109.5
N4—N3—H3	121.6	H10B—C10—H10C	109.5
C1—N3—H3	121.6	N4—C11—C12	115.4 (3)
C11—N4—N3	120.2 (3)	N4—C11—C10	122.7 (3)
C18—N5—C19	120.2 (3)	C12—C11—C10	121.8 (3)
C18—N5—C20	121.3 (3)	C17—C12—C13	116.4 (3)
C19—N5—C20	118.5 (3)	C17—C12—C11	121.2 (3)
C5—O2—H2A	109.5	C13—C12—C11	122.4 (3)
C13—O3—H3A	109.5	O3—C13—C14	117.2 (3)
O1—C1—N1	124.8 (3)	O3—C13—C12	122.7 (3)
O1—C1—N3	123.5 (3)	C14—C13—C12	120.1 (3)
N1—C1—N3	111.6 (3)	C15—C14—C13	121.2 (4)
C3—C2—H2B	109.5	C15—C14—H14	119.4
C3—C2—H2C	109.5	C13—C14—H14	119.4
H2B—C2—H2C	109.5	C14—C15—C16	119.7 (4)
C3—C2—H2D	109.5	C14—C15—CG1	59.7 (2)
H2B—C2—H2D	109.5	C14—C15—H15	120.2
H2C—C2—H2D	109.5	C16—C15—H15	120.2
N2—C3—C4	115.1 (3)	C15—C16—C17	120.0 (4)
N2—C3—C2	123.6 (3)	C15—C16—H16	120.0
C4—C3—C2	121.3 (3)	C17—C16—H16	120.0
C9—C4—C5	116.9 (3)	C16—C17—C12	122.5 (4)
C9—C4—C3	120.9 (3)	C16—C17—H17	118.8
C5—C4—C3	122.2 (3)	C12—C17—H17	118.8
O2—C5—C6	116.4 (3)	O4—C18—N5	125.4 (4)
O2—C5—C4	123.3 (3)	O4—C18—H18	117.3
C6—C5—C4	120.3 (3)	N5—C18—H18	117.3
C7—C6—C5	121.0 (3)	N5—C19—H19A	109.5
C7—C6—H6	119.5	N5—C19—H19B	109.5
C5—C6—H6	119.5	H19A—C19—H19B	109.5
C6—C7—C8	119.6 (3)	N5—C19—H19C	109.5
C6—C7—H7	120.2	H19A—C19—H19C	109.5
C8—C7—H7	120.2	H19B—C19—H19C	109.5
C7—C8—C9	120.0 (4)	N5—C20—H20A	109.5
C7—C8—H8	120.0	N5—C20—H20B	109.5
C9—C8—H8	120.0	H20A—C20—H20B	109.5
C8—C9—C4	122.2 (3)	N5—C20—H20C	109.5
C8—C9—H9	118.9	H20A—C20—H20C	109.5
C4—C9—H9	118.9	H20B—C20—H20C	109.5

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C12–C17 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.86	2.02	2.805 (3)	151
N3—H3···O4	0.86	2.09	2.858 (4)	148
O2—H2A···N2	0.82	1.83	2.548 (3)	145
O3—H3A···N4	0.82	1.83	2.546 (3)	145
C6—H6···O1ⁱ	0.93	2.57	3.241 (4)	129
C10—H10A···Cgⁱⁱ	0.96	2.66	3.536 (4)	153

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈N₄O₃·C₃H₇NO
M_r	399.45
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	16.6372 (15), 7.5880 (9), 16.2967 (14)
β (°)	94.472 (1)
V (Å³)	2051.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.47 × 0.46 × 0.23

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.958, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	10277, 3596, 1712
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.165, 1.04
No. of reflections	3596
No. of parameters	263
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.17

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

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C12–C17 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.86	2.02	2.805 (3)	151.3
N3—H3···O4	0.86	2.09	2.858 (4)	148.2
O2—H2A···N2	0.82	1.83	2.548 (3)	144.6
O3—H3A···N4	0.82	1.83	2.546 (3)	145.1
C6—H6···O1ⁱ	0.93	2.57	3.241 (4)	128.9
C10—H10A···Cgⁱⁱ	0.96	2.66	3.536 (4)	152.6

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

Acknowledgements

The authors acknowledge financial support by the Science Foundation of China (grant No. 20877037).

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, M. X., Cai, P., Duan, C. Y., Lu, F., Xie, J. & Meng, Q. J. (2004). Inorg. Chem. 43, 5174–5176. Web of Science CSD CrossRef PubMed CAS Google Scholar
Loncle, C., Brunel, J. M., Vidal, N., Dherbomez, M. & Letourneux, Y. (2004). Eur. J. Med. Chem. 39, 1067–1071. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zukerman-Schpector, J., Affan, M. A., Foo, S. W. & Tiekink, E. R. T. (2009). Acta Cryst. E65, o2951. Web of Science CrossRef IUCr Journals Google Scholar

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Volume 66| Part 10| October 2010| Page o2645

doi:10.1107/S1600536810037517

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

1,5-Bis­[1-(2-hy­dr­oxy­phen­yl)ethyl­­idene]carbonohydrazide di­methyl­formamide monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1,5-Bis[1-(2-hydroxyphenyl)ethylidene]carbonohydrazide dimethylformamide monosolvate