1,5-Bis-[1-(2-hy-droxy-phen-yl)ethyl-idene]carbonohydrazide dimethyl-formamide monosolvate.

In the title compound, C(17)H(18)N(4)O(3)·C(3)H(7)NO, the main disubstituted urea and solvate mol-ecules are linked by pairs of N-H⋯O hydrogen bonds. In the main mol-ecules, the benzene rings form a dihedral angle of 15.59 (13)° a;nd two intra-molecular O-H⋯N hydrogen bonds influence the mol-ecular conformation. In the crystal structure, weak inter-molecular C-H⋯O inter-actions link the hydrogen-bonded pairs into chains along the b axis. The chains associate via C-H⋯π inter-actions.

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 = 399.45

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.165

S = 1.04

3596 reflections

263 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.17 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/S1600536810037517/cv2762sup1.cif

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

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

C17H18N4O3·C3H7NO	F(000) = 848
Mr = 399.45	Dx = 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

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

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(Fo2) + (0.0542P)2 + 0.8303P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3596 reflections	Δρmax = 0.22 e Å−3
263 parameters	Δρmin = −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)

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
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*

	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)

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

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

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) ; (ii) .