1,5-Bis[1-(2,4-dihy­droxy­phen­yl)ethyl­idene]carbonohydrazide dimethyl­formamide disolvate

He, Q.-P.; Tan, B.; Lu, Z.-H.

doi:10.1107/S1600536810043151

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2968

https://doi.org/10.1107/S1600536810043151

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1,5-Bis[1-(2,4-dihydroxyphenyl)ethylidene]carbonohydrazide dimethylformamide disolvate

Qing-Peng He,^a ^* Bo Tan ^a and Ze-Hua Lu ^b

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China, and ^bLiaocheng International Peace Hospital, Shandong 252059, People's Republic of China
^*Correspondence e-mail: heqp2008@163.com

(Received 15 October 2010; accepted 22 October 2010; online 30 October 2010)

In the title compound, C₁₇H₁₈N₄O₅·2C₃H₇NO, two solvent molecules are linked to the main molecule via N—H⋯O and O—H⋯O hydrogen bonds, forming a hydrogen-bonded trimer. Intramolecular O—H⋯N hydrogen bonds influence the molecular conformation of the main molecule, and the two benzene rings form a dihedral angle of 10.55 (18)°. In the crystal, intermolecular O—H⋯O hydrogen bonds link hydrogen-bonded trimers into ribbons extending along the b axis.

Related literature

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

Experimental

Crystal data

C₁₇H₁₈N₄O₅·2C₃H₇NO
M_r = 504.55
Monoclinic, P 2₁ /n
a = 11.3506 (11) Å
b = 9.0160 (7) Å
c = 24.953 (3) Å
β = 97.546 (1)°
V = 2531.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.50 × 0.37 × 0.35 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.952, T_max = 0.966
12361 measured reflections
4466 independent reflections
2158 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.152
S = 1.03
4466 reflections
331 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.83	2.549 (3)	145
O3—H3⋯N4	0.82	1.84	2.562 (3)	146
O2—H2⋯O7	0.82	1.90	2.704 (4)	168
N2—H2′⋯O6	0.86	2.13	2.918 (3)	153
N3—H3′⋯O6	0.86	2.16	2.932 (3)	149
O4—H4⋯O5ⁱ	0.82	1.86	2.680 (3)	173
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: https://doi.org/10.1107/S1600536810043151/cv2779sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810043151/cv2779Isup2.hkl

checkCIF report

Comment top

Carbonohydrazide Schiff base derivatives are known to exhibit a wide range of interesting biological activities, including antibacterial antifungal, anticonvulsant, anticancer activities as well as herbicidal and fungicidal activity (Loncle et al., 2004; Li et al., 2004). Herewith we present the crystal structure of the title compound (I) - a new carbonohydrazide derivative.

In (I) (Fig. 1), the bond lengths and angles of the main molecule 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 intramolecular O—H···N hydrogen bonds (Table 1) influence the molecular conformation. Two DMF solvent molecules are linked to the main molecule via N—H···O and O—H···O hydrogen bonds (Table 1) forming a hydrogen-bonded trimer (Fig. 1). Intermolecular O—H···O hydrogen bonds (Table 1) link hydrogen-bonded trimers into ribbons extended along the b axis.

Related literature top

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

Experimental top

2, 4-Dihydroxylacetophenone (10.0 mmol) and carbohydrazide (5.0 mmol) were mixed in 50 ml flash. After 3h stirring at 373 K, the resulting mixture was cooled to room temperature, and recrystalized from DMF, and afforded the title compound as a crystalline solid.

Structure description top

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

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. Dashed lines denote intermolecular hydrogen bonds.

1,5-Bis[1-(2,4-dihydroxyphenyl)ethylidene]carbonohydrazide dimethylformamide disolvate top

Crystal data top

C₁₇H₁₈N₄O₅·2C₃H₇NO	F(000) = 1072
M_r = 504.55	D_x = 1.324 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.3506 (11) Å	Cell parameters from 2127 reflections
b = 9.0160 (7) Å	θ = 2.9–23.9°
c = 24.953 (3) Å	µ = 0.10 mm⁻¹
β = 97.546 (1)°	T = 298 K
V = 2531.5 (4) Å³	Block, colourless
Z = 4	0.50 × 0.37 × 0.35 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4466 independent reflections
Radiation source: fine-focus sealed tube	2158 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
φ and ω scans	θ_max = 25.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→13
T_min = 0.952, T_max = 0.966	k = −10→10
12361 measured reflections	l = −29→27

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.152	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0565P)² + 0.4683P] where P = (F_o² + 2F_c²)/3
4466 reflections	(Δ/σ)_max = 0.009
331 parameters	Δρ_max = 0.30 e Å⁻³
1 restraint	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₇H₁₈N₄O₅·2C₃H₇NO	V = 2531.5 (4) Å³
M_r = 504.55	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.3506 (11) Å	µ = 0.10 mm⁻¹
b = 9.0160 (7) Å	T = 298 K
c = 24.953 (3) Å	0.50 × 0.37 × 0.35 mm
β = 97.546 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4466 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2158 reflections with I > 2σ(I)
T_min = 0.952, T_max = 0.966	R_int = 0.055
12361 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	1 restraint
wR(F²) = 0.152	H-atom parameters constrained
S = 1.03	Δρ_max = 0.30 e Å⁻³
4466 reflections	Δρ_min = −0.27 e Å⁻³
331 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
N3	0.5482 (2)	1.0132 (3)	0.38574 (9)	0.0413 (7)
H3'	0.6233	1.0203	0.3961	0.050*
N4	0.4960 (2)	1.0910 (3)	0.34129 (9)	0.0379 (7)
N1	0.4829 (2)	0.7684 (3)	0.48746 (9)	0.0362 (7)
N2	0.5404 (2)	0.8673 (3)	0.45843 (9)	0.0375 (7)
H2'	0.6131	0.8921	0.4687	0.045*
C1	0.4790 (3)	0.9250 (4)	0.41282 (12)	0.0352 (8)
C2	0.5629 (3)	1.1733 (4)	0.31528 (12)	0.0371 (8)
O1	0.29729 (18)	0.6107 (3)	0.49012 (9)	0.0542 (7)
H1	0.3414	0.6680	0.4767	0.081*
O4	0.34283 (19)	1.5034 (3)	0.13770 (9)	0.0537 (7)
H4	0.2743	1.4758	0.1286	0.081*
C4	0.5033 (3)	1.2567 (4)	0.26924 (11)	0.0346 (8)
C12	0.4686 (3)	0.6037 (3)	0.55900 (11)	0.0348 (8)
O5	0.37418 (19)	0.8984 (3)	0.39800 (9)	0.0519 (7)
C10	0.5368 (3)	0.7104 (3)	0.53123 (12)	0.0353 (8)
C7	0.3926 (3)	1.4211 (4)	0.18086 (12)	0.0405 (8)
C6	0.3283 (3)	1.3208 (4)	0.20663 (12)	0.0406 (8)
H14	0.2480	1.3068	0.1946	0.049*
O3	0.31113 (19)	1.1458 (3)	0.27370 (9)	0.0607 (7)
H3	0.3505	1.1027	0.2989	0.091*
C14	0.2910 (3)	0.4568 (4)	0.56516 (13)	0.0465 (9)
H16	0.2140	0.4307	0.5509	0.056*
C13	0.3532 (3)	0.5593 (4)	0.53799 (12)	0.0391 (8)
C9	0.5651 (3)	1.3599 (4)	0.24144 (13)	0.0476 (9)
H18	0.6457	1.3738	0.2526	0.057*
C5	0.3820 (3)	1.2408 (4)	0.25034 (12)	0.0378 (8)
C17	0.5158 (3)	0.5373 (4)	0.60781 (13)	0.0472 (9)
H20	0.5923	0.5634	0.6228	0.057*
C15	0.3419 (3)	0.3934 (4)	0.61297 (14)	0.0460 (9)
C16	0.4555 (3)	0.4360 (4)	0.63457 (13)	0.0500 (9)
H22	0.4906	0.3958	0.6671	0.060*
O2	0.2771 (2)	0.2926 (3)	0.63652 (10)	0.0647 (7)
H2	0.3137	0.2667	0.6655	0.097*
C8	0.5119 (3)	1.4409 (4)	0.19856 (13)	0.0482 (9)
H24	0.5560	1.5090	0.1815	0.058*
C11	0.6630 (3)	0.7461 (4)	0.55445 (13)	0.0512 (9)
H26A	0.6754	0.8512	0.5530	0.077*
H26B	0.7168	0.6964	0.5338	0.077*
H26C	0.6771	0.7133	0.5913	0.077*
C3	0.6951 (3)	1.1842 (4)	0.33107 (14)	0.0601 (11)
H32A	0.7117	1.2473	0.3621	0.090*
H32B	0.7310	1.2250	0.3016	0.090*
H32C	0.7271	1.0872	0.3396	0.090*
O6	0.7696 (2)	1.0156 (3)	0.46093 (10)	0.0652 (8)
C18	0.8226 (3)	1.0859 (4)	0.49864 (15)	0.0531 (10)
H18A	0.7916	1.0823	0.5313	0.064*
N5	0.9189 (2)	1.1658 (3)	0.49747 (12)	0.0555 (8)
C20	0.9664 (4)	1.1869 (5)	0.44770 (17)	0.0911 (15)
H20A	0.9235	1.1262	0.4201	0.137*
H20B	1.0488	1.1594	0.4523	0.137*
H20C	0.9587	1.2893	0.4372	0.137*
C19	0.9714 (4)	1.2474 (5)	0.54508 (17)	0.0898 (15)
H19A	0.9311	1.2217	0.5753	0.135*
H19B	0.9636	1.3519	0.5383	0.135*
H19C	1.0540	1.2222	0.5530	0.135*
N6	0.5058 (3)	0.0928 (4)	0.80215 (12)	0.0562 (8)
C23	0.4210 (3)	−0.0012 (4)	0.82410 (14)	0.0664 (11)
H23A	0.3454	0.0059	0.8019	0.100*
H23B	0.4130	0.0302	0.8602	0.100*
H23C	0.4482	−0.1020	0.8247	0.100*
C22	0.4740 (4)	0.1708 (5)	0.75761 (18)	0.0661 (11)
H22A	0.5326	0.2278	0.7448	0.079*
C21	0.6253 (3)	0.0985 (5)	0.83068 (17)	0.0882 (14)
H21A	0.6726	0.1650	0.8123	0.132*
H21B	0.6598	0.0011	0.8318	0.132*
H21C	0.6228	0.1332	0.8669	0.132*
O7	0.3748 (2)	0.1750 (3)	0.73179 (11)	0.0717 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N3	0.0364 (15)	0.0483 (19)	0.0378 (15)	0.0007 (14)	−0.0007 (12)	0.0098 (14)
N4	0.0402 (15)	0.0406 (18)	0.0319 (15)	0.0063 (14)	0.0004 (12)	0.0065 (13)
N1	0.0425 (16)	0.0320 (17)	0.0338 (15)	0.0011 (13)	0.0043 (13)	0.0017 (13)
N2	0.0347 (14)	0.0403 (18)	0.0360 (15)	−0.0025 (13)	−0.0015 (12)	0.0051 (13)
C1	0.040 (2)	0.032 (2)	0.0328 (18)	0.0046 (16)	0.0008 (16)	−0.0022 (16)
C2	0.0377 (18)	0.042 (2)	0.0318 (18)	−0.0001 (17)	0.0061 (15)	−0.0038 (16)
O1	0.0406 (13)	0.0608 (19)	0.0587 (16)	−0.0030 (12)	−0.0026 (12)	0.0149 (13)
O4	0.0482 (14)	0.0626 (18)	0.0477 (14)	0.0000 (13)	−0.0038 (11)	0.0189 (13)
C4	0.0378 (18)	0.037 (2)	0.0282 (17)	0.0016 (16)	0.0029 (14)	−0.0016 (15)
C12	0.0416 (19)	0.030 (2)	0.0327 (18)	0.0023 (16)	0.0054 (15)	−0.0018 (15)
O5	0.0396 (13)	0.0582 (17)	0.0542 (14)	−0.0065 (12)	−0.0077 (11)	0.0107 (12)
C10	0.0405 (18)	0.030 (2)	0.0348 (18)	0.0011 (16)	0.0024 (15)	−0.0051 (16)
C7	0.0394 (19)	0.047 (2)	0.0347 (18)	0.0055 (17)	0.0017 (15)	0.0038 (17)
C6	0.0298 (17)	0.048 (2)	0.0434 (19)	−0.0005 (17)	0.0016 (15)	0.0085 (18)
O3	0.0432 (14)	0.072 (2)	0.0669 (18)	−0.0047 (14)	0.0067 (12)	0.0319 (14)
C14	0.042 (2)	0.042 (2)	0.057 (2)	−0.0006 (17)	0.0128 (17)	0.0010 (19)
C13	0.0417 (19)	0.036 (2)	0.0395 (19)	0.0052 (17)	0.0044 (16)	−0.0005 (16)
C9	0.0382 (19)	0.059 (3)	0.044 (2)	−0.0081 (18)	−0.0004 (16)	0.0053 (19)
C5	0.0373 (19)	0.041 (2)	0.0373 (18)	0.0001 (17)	0.0119 (15)	0.0050 (16)
C17	0.051 (2)	0.045 (2)	0.045 (2)	−0.0019 (18)	0.0012 (17)	−0.0013 (18)
C15	0.056 (2)	0.038 (2)	0.049 (2)	0.0041 (19)	0.0249 (19)	0.0009 (18)
C16	0.065 (2)	0.047 (2)	0.039 (2)	0.000 (2)	0.0053 (18)	0.0057 (18)
O2	0.0669 (17)	0.0618 (19)	0.0703 (19)	−0.0031 (15)	0.0271 (13)	0.0148 (15)
C8	0.042 (2)	0.054 (3)	0.047 (2)	−0.0096 (18)	0.0022 (16)	0.0161 (19)
C11	0.049 (2)	0.051 (2)	0.050 (2)	−0.0088 (18)	−0.0045 (16)	0.0054 (18)
C3	0.043 (2)	0.080 (3)	0.055 (2)	−0.005 (2)	−0.0022 (17)	0.019 (2)
O6	0.0573 (16)	0.076 (2)	0.0581 (16)	−0.0114 (15)	−0.0095 (13)	−0.0035 (15)
C18	0.047 (2)	0.061 (3)	0.051 (2)	−0.001 (2)	0.0053 (18)	0.008 (2)
N5	0.0405 (17)	0.061 (2)	0.065 (2)	−0.0069 (16)	0.0060 (15)	0.0056 (18)
C20	0.069 (3)	0.113 (4)	0.096 (3)	−0.006 (3)	0.025 (3)	0.036 (3)
C19	0.079 (3)	0.084 (4)	0.099 (3)	−0.032 (3)	−0.016 (3)	−0.016 (3)
N6	0.054 (2)	0.055 (2)	0.060 (2)	−0.0052 (17)	0.0098 (16)	−0.0024 (18)
C23	0.079 (3)	0.063 (3)	0.061 (2)	−0.005 (2)	0.025 (2)	0.005 (2)
C22	0.073 (3)	0.055 (3)	0.076 (3)	−0.007 (2)	0.033 (2)	0.000 (2)
C21	0.072 (3)	0.099 (4)	0.089 (3)	−0.017 (3)	−0.004 (2)	−0.012 (3)
O7	0.0652 (18)	0.078 (2)	0.0736 (19)	0.0075 (16)	0.0137 (15)	0.0123 (16)

Geometric parameters (Å, º) top

N3—C1	1.358 (4)	C15—O2	1.352 (4)
N3—N4	1.379 (3)	C15—C16	1.385 (4)
N3—H3'	0.8600	C16—H22	0.9300
N4—C2	1.295 (4)	O2—H2	0.8200
N1—C10	1.291 (3)	C8—H24	0.9300
N1—N2	1.368 (3)	C11—H26A	0.9600
N2—C1	1.358 (3)	C11—H26B	0.9600
N2—H2'	0.8600	C11—H26C	0.9600
C1—O5	1.223 (3)	C3—H32A	0.9600
C2—C4	1.462 (4)	C3—H32B	0.9600
C2—C3	1.504 (4)	C3—H32C	0.9600
O1—C13	1.359 (3)	O6—C18	1.225 (4)
O1—H1	0.8200	C18—N5	1.312 (4)
O4—C7	1.367 (3)	C18—H18A	0.9300
O4—H4	0.8200	N5—C20	1.430 (4)
C4—C9	1.402 (4)	N5—C19	1.456 (4)
C4—C5	1.403 (4)	C20—H20A	0.9600
C12—C17	1.400 (4)	C20—H20B	0.9600
C12—C13	1.403 (4)	C20—H20C	0.9600
C12—C10	1.465 (4)	C19—H19A	0.9600
C10—C11	1.507 (4)	C19—H19B	0.9600
C7—C6	1.374 (4)	C19—H19C	0.9600
C7—C8	1.380 (4)	N6—C22	1.325 (5)
C6—C5	1.381 (4)	N6—C23	1.443 (4)
C6—H14	0.9300	N6—C21	1.447 (4)
O3—C5	1.358 (3)	C23—H23A	0.9600
O3—H3	0.8200	C23—H23B	0.9600
C14—C15	1.380 (4)	C23—H23C	0.9600
C14—C13	1.392 (4)	C22—O7	1.222 (4)
C14—H16	0.9300	C22—H22A	0.9300
C9—C8	1.369 (4)	C21—H21A	0.9600
C9—H18	0.9300	C21—H21B	0.9600
C17—C16	1.367 (4)	C21—H21C	0.9600
C17—H20	0.9300

C1—N3—N4	118.9 (2)	C15—O2—H2	109.5
C1—N3—H3'	120.6	C9—C8—C7	119.6 (3)
N4—N3—H3'	120.6	C9—C8—H24	120.2
C2—N4—N3	118.5 (3)	C7—C8—H24	120.2
C10—N1—N2	120.4 (2)	C10—C11—H26A	109.5
C1—N2—N1	117.7 (3)	C10—C11—H26B	109.5
C1—N2—H2'	121.1	H26A—C11—H26B	109.5
N1—N2—H2'	121.1	C10—C11—H26C	109.5
O5—C1—N3	124.6 (3)	H26A—C11—H26C	109.5
O5—C1—N2	123.4 (3)	H26B—C11—H26C	109.5
N3—C1—N2	112.0 (3)	C2—C3—H32A	109.5
N4—C2—C4	116.5 (3)	C2—C3—H32B	109.5
N4—C2—C3	122.5 (3)	H32A—C3—H32B	109.5
C4—C2—C3	121.0 (3)	C2—C3—H32C	109.5
C13—O1—H1	109.5	H32A—C3—H32C	109.5
C7—O4—H4	109.5	H32B—C3—H32C	109.5
C9—C4—C5	115.7 (3)	O6—C18—N5	126.4 (4)
C9—C4—C2	121.3 (3)	O6—C18—H18A	116.8
C5—C4—C2	123.0 (3)	N5—C18—H18A	116.8
C17—C12—C13	115.8 (3)	C18—N5—C20	120.1 (3)
C17—C12—C10	121.8 (3)	C18—N5—C19	120.8 (3)
C13—C12—C10	122.4 (3)	C20—N5—C19	118.7 (3)
N1—C10—C12	116.4 (3)	N5—C20—H20A	109.5
N1—C10—C11	124.1 (3)	N5—C20—H20B	109.5
C12—C10—C11	119.6 (3)	H20A—C20—H20B	109.5
C6—C7—O4	122.4 (3)	N5—C20—H20C	109.5
C6—C7—C8	119.7 (3)	H20A—C20—H20C	109.5
O4—C7—C8	117.9 (3)	H20B—C20—H20C	109.5
C7—C6—C5	120.4 (3)	N5—C19—H19A	109.5
C7—C6—H14	119.8	N5—C19—H19B	109.5
C5—C6—H14	119.8	H19A—C19—H19B	109.5
C5—O3—H3	109.5	N5—C19—H19C	109.5
C15—C14—C13	121.0 (3)	H19A—C19—H19C	109.5
C15—C14—H16	119.5	H19B—C19—H19C	109.5
C13—C14—H16	119.5	C22—N6—C23	120.5 (3)
O1—C13—C14	116.5 (3)	C22—N6—C21	121.9 (4)
O1—C13—C12	122.4 (3)	C23—N6—C21	117.6 (3)
C14—C13—C12	121.1 (3)	N6—C23—H23A	109.5
C8—C9—C4	122.9 (3)	N6—C23—H23B	109.5
C8—C9—H18	118.5	H23A—C23—H23B	109.5
C4—C9—H18	118.5	N6—C23—H23C	109.5
O3—C5—C6	116.3 (3)	H23A—C23—H23C	109.5
O3—C5—C4	122.1 (3)	H23B—C23—H23C	109.5
C6—C5—C4	121.6 (3)	O7—C22—N6	126.1 (4)
C16—C17—C12	123.5 (3)	O7—C22—H22A	116.9
C16—C17—H20	118.2	N6—C22—H22A	116.9
C12—C17—H20	118.2	N6—C21—H21A	109.5
O2—C15—C14	117.7 (3)	N6—C21—H21B	109.5
O2—C15—C16	123.3 (3)	H21A—C21—H21B	109.5
C14—C15—C16	119.0 (3)	N6—C21—H21C	109.5
C17—C16—C15	119.7 (3)	H21A—C21—H21C	109.5
C17—C16—H22	120.2	H21B—C21—H21C	109.5
C15—C16—H22	120.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.83	2.549 (3)	145
O3—H3···N4	0.82	1.84	2.562 (3)	146
O2—H2···O7	0.82	1.90	2.704 (4)	168
N2—H2′···O6	0.86	2.13	2.918 (3)	153
N3—H3′···O6	0.86	2.16	2.932 (3)	149
O4—H4···O5ⁱ	0.82	1.86	2.680 (3)	173

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈N₄O₅·2C₃H₇NO
M_r	504.55
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	11.3506 (11), 9.0160 (7), 24.953 (3)
β (°)	97.546 (1)
V (Å³)	2531.5 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.50 × 0.37 × 0.35

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.952, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	12361, 4466, 2158
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.152, 1.03
No. of reflections	4466
No. of parameters	331
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.27

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
O1—H1···N1	0.82	1.83	2.549 (3)	145.2
O3—H3···N4	0.82	1.84	2.562 (3)	145.5
O2—H2···O7	0.82	1.90	2.704 (4)	168
N2—H2'···O6	0.86	2.13	2.918 (3)	153
N3—H3'···O6	0.86	2.16	2.932 (3)	149
O4—H4···O5ⁱ	0.82	1.86	2.680 (3)	173.2

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

Acknowledgements

This project was supported by the University Student Science and Technology Culture Foundation of Liaocheng University (grant No. SRT10056HX2) and the Foundation of Liaocheng University (grant No. X09010).

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

1,5-Bis[1-(2,4-dihy­dr­oxy­phen­yl)ethyl­­idene]carbonohydrazide di­methyl­formamide disolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1,5-Bis[1-(2,4-dihydroxyphenyl)ethylidene]carbonohydrazide dimethylformamide disolvate