1,5-Bis[1-(2,4-dihy-droxy-phen-yl)ethyl-idene]carbonohydrazide dimethyl-formamide disolvate.

In the title compound, C(17)H(18)N(4)O(5)·2C(3)H(7)NO, two solvent mol-ecules are linked to the main mol-ecule via N-H⋯O and O-H⋯O hydrogen bonds, forming a hydrogen-bonded trimer. Intra-molecular O-H⋯N hydrogen bonds influence the mol-ecular conformation of the main mol-ecule, and the two benzene rings form a dihedral angle of 10.55 (18)°. In the crystal, inter-molecular 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 = 504.55

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.152

S = 1.03

4466 reflections

331 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.27 e Å−3

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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810043151/cv2779sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043151/cv2779Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H18N4O5·2C3H7NO	F(000) = 1072
Mr = 504.55	Dx = 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

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

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(Fo2) + (0.0565P)2 + 0.4683P] where P = (Fo2 + 2Fc2)/3
4466 reflections	(Δ/σ)max = 0.009
331 parameters	Δρmax = 0.30 e Å−3
1 restraint	Δρmin = −0.27 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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

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

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) .