N'-[(E)-4-Benz-yloxy-2-hy-droxy-benzyl-idene]-4-nitro-benzohydrazide di-methyl-formamide monosolvate.

The title compound, C21H17N3O5·C3H7NO, exists in an E conformation with respect to the azomethine double bond of the hydrazide mol-ecule. This mol-ecule contains an intra-molecular O-H⋯N hydrogen bond, while an inter-molecular N-H⋯O hydrogen bond links the hydrazide to the formamide mol-ecule of solvation. Nonclassical C-H⋯O inter-molecular hydrogen bonds build up a supra-molecular architecture, together with two C-H⋯π inter-actions and a weak π-π inter-action, with a centroid-centroid distance of 3.650 (13) Å.

Related literature

For the biological and analytical applications of carbohydrazides, see: Vicini et al. (2002 ▶); Savini et al. (2002 ▶); Grande et al. (2007 ▶). For the synthesis of related compounds, see: Mathew & Kurup (2011 ▶); Despaigne et al. (2009 ▶). For related structures, see: Joseph et al. (2012 ▶).

Experimental

Crystal data

C21H17N3O5·C3H7NO

M = 464.47

Monoclinic,

a = 10.0160 (8) Å

b = 22.661 (2) Å

c = 10.2611 (11) Å

β = 101.392 (5)°

V = 2283.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.40 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.977, T max = 0.981

16107 measured reflections

4910 independent reflections

2901 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.176

S = 1.04

4910 reflections

318 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813017091/fj2634sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813017091/fj2634Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813017091/fj2634Isup3.cml

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

C21H17N3O5·C3H7NO	F(000) = 976
Mr = 464.47	Dx = 1.351 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3347 reflections
a = 10.0160 (8) Å	θ = 2.7–27.6°
b = 22.661 (2) Å	µ = 0.10 mm−1
c = 10.2611 (11) Å	T = 296 K
β = 101.392 (5)°	Block, yellow
V = 2283.1 (4) Å3	0.40 × 0.20 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	4910 independent reflections
Radiation source: fine-focus sealed tube	2901 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω and φ scan	θmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→11
Tmin = 0.977, Tmax = 0.981	k = −28→28
16107 measured reflections	l = −13→8

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)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.176	w = 1/[σ2(Fo2) + (0.0894P)2 + 0.2279P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
4910 reflections	Δρmax = 0.40 e Å−3
318 parameters	Δρmin = −0.22 e Å−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0078 (15)

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
O1	0.07170 (14)	−0.02077 (7)	0.19458 (16)	0.0520 (4)
O2	0.50913 (16)	0.05541 (8)	0.38186 (17)	0.0554 (5)
O3	0.87382 (16)	0.10480 (8)	0.40720 (18)	0.0605 (5)
O4	1.4753 (2)	0.21761 (12)	0.2984 (3)	0.1028 (9)
O5	1.4051 (2)	0.21112 (11)	0.0893 (3)	0.0926 (8)
O6	0.7557 (2)	0.15662 (12)	−0.0661 (2)	0.0952 (8)
N1	0.65997 (16)	0.08803 (8)	0.2177 (2)	0.0430 (5)
N2	0.77984 (17)	0.10975 (8)	0.1910 (2)	0.0435 (5)
N3	1.3896 (2)	0.20500 (9)	0.2026 (3)	0.0619 (6)
N4	0.71736 (19)	0.18185 (9)	−0.2805 (2)	0.0540 (5)
C1	−0.0899 (2)	−0.12417 (10)	0.2521 (3)	0.0543 (6)
H1	−0.0142	−0.1398	0.2244	0.065*
C2	−0.2068 (3)	−0.15693 (11)	0.2395 (3)	0.0631 (7)
H2A	−0.2098	−0.1947	0.2036	0.076*
C3	−0.3193 (2)	−0.13453 (11)	0.2792 (3)	0.0574 (7)
H3	−0.3983	−0.1570	0.2701	0.069*
C4	−0.3152 (2)	−0.07925 (11)	0.3320 (3)	0.0544 (6)
H4	−0.3911	−0.0639	0.3599	0.065*
C5	−0.1976 (2)	−0.04604 (10)	0.3440 (2)	0.0453 (6)
H5	−0.1955	−0.0081	0.3787	0.054*
C6	−0.0841 (2)	−0.06820 (9)	0.3056 (2)	0.0407 (5)
C7	0.0453 (2)	−0.03359 (10)	0.3232 (2)	0.0459 (6)
H7A	0.0366	0.0028	0.3707	0.055*
H7B	0.1199	−0.0563	0.3742	0.055*
C8	0.19366 (19)	0.00386 (9)	0.1859 (2)	0.0389 (5)
C9	0.2933 (2)	0.01794 (9)	0.2933 (2)	0.0407 (5)
H9	0.2796	0.0112	0.3791	0.049*
C10	0.41497 (19)	0.04237 (9)	0.2735 (2)	0.0378 (5)
C11	0.43622 (19)	0.05309 (9)	0.1444 (2)	0.0370 (5)
C12	0.3322 (2)	0.03864 (10)	0.0385 (2)	0.0438 (5)
H12	0.3443	0.0459	−0.0477	0.053*
C13	0.2125 (2)	0.01410 (10)	0.0570 (2)	0.0443 (5)
H13	0.1446	0.0044	−0.0156	0.053*
C14	0.5624 (2)	0.07781 (9)	0.1208 (2)	0.0413 (5)
H14	0.5722	0.0862	0.0344	0.050*
C15	0.8836 (2)	0.11689 (9)	0.2939 (2)	0.0409 (5)
C16	1.0138 (2)	0.14008 (9)	0.2640 (2)	0.0389 (5)
C17	1.1128 (2)	0.15662 (10)	0.3697 (3)	0.0504 (6)
H17	1.0960	0.1535	0.4554	0.060*
C18	1.2367 (2)	0.17777 (11)	0.3517 (3)	0.0536 (6)
H18	1.3035	0.1890	0.4239	0.064*
C19	1.2585 (2)	0.18182 (9)	0.2247 (3)	0.0456 (6)
C20	1.1643 (2)	0.16467 (12)	0.1179 (3)	0.0596 (7)
H20	1.1825	0.1672	0.0326	0.072*
C21	1.0410 (2)	0.14332 (12)	0.1380 (3)	0.0566 (7)
H21	0.9756	0.1310	0.0656	0.068*
C22	0.7086 (3)	0.14686 (13)	−0.1811 (4)	0.0675 (8)
H22	0.6620	0.1115	−0.2011	0.081*
C23	0.6524 (4)	0.1653 (2)	−0.4133 (4)	0.1072 (13)
H23A	0.6184	0.1257	−0.4128	0.161*
H23B	0.7172	0.1674	−0.4706	0.161*
H23C	0.5782	0.1917	−0.4450	0.161*
C24	0.7845 (4)	0.23712 (15)	−0.2607 (5)	0.1139 (15)
H24A	0.8578	0.2379	−0.3085	0.171*
H24B	0.8202	0.2428	−0.1676	0.171*
H24C	0.7210	0.2681	−0.2927	0.171*
H2'	0.784 (2)	0.1204 (10)	0.1096 (12)	0.046 (7)*
H2O	0.580 (2)	0.0665 (14)	0.355 (3)	0.101 (12)*

	U11	U22	U33	U12	U13	U23
O1	0.0393 (8)	0.0784 (11)	0.0368 (10)	−0.0205 (7)	0.0040 (7)	0.0106 (8)
O2	0.0456 (9)	0.0794 (12)	0.0386 (10)	−0.0217 (8)	0.0021 (8)	0.0011 (9)
O3	0.0497 (9)	0.0889 (13)	0.0435 (11)	−0.0115 (8)	0.0101 (8)	0.0135 (10)
O4	0.0555 (12)	0.156 (2)	0.093 (2)	−0.0442 (13)	0.0046 (12)	0.0068 (17)
O5	0.0732 (14)	0.1240 (19)	0.0883 (19)	−0.0293 (12)	0.0346 (13)	0.0187 (15)
O6	0.0904 (16)	0.135 (2)	0.0553 (15)	0.0031 (13)	0.0032 (13)	0.0299 (15)
N1	0.0351 (9)	0.0479 (10)	0.0477 (13)	−0.0049 (7)	0.0121 (9)	0.0053 (9)
N2	0.0372 (9)	0.0523 (11)	0.0428 (13)	−0.0069 (8)	0.0121 (9)	0.0068 (10)
N3	0.0455 (12)	0.0616 (13)	0.0805 (19)	−0.0063 (9)	0.0169 (13)	0.0116 (13)
N4	0.0539 (11)	0.0587 (12)	0.0504 (14)	0.0043 (9)	0.0130 (10)	0.0082 (11)
C1	0.0560 (14)	0.0531 (14)	0.0583 (18)	−0.0020 (11)	0.0222 (13)	−0.0001 (12)
C2	0.0785 (18)	0.0465 (13)	0.069 (2)	−0.0189 (12)	0.0264 (16)	−0.0068 (13)
C3	0.0500 (13)	0.0650 (16)	0.0575 (18)	−0.0217 (11)	0.0111 (12)	0.0049 (14)
C4	0.0387 (12)	0.0662 (16)	0.0592 (18)	−0.0036 (10)	0.0115 (12)	0.0052 (13)
C5	0.0458 (12)	0.0472 (12)	0.0432 (15)	−0.0044 (9)	0.0094 (10)	0.0019 (11)
C6	0.0391 (11)	0.0490 (12)	0.0335 (13)	−0.0055 (9)	0.0056 (9)	0.0066 (10)
C7	0.0397 (11)	0.0599 (14)	0.0375 (14)	−0.0100 (9)	0.0064 (10)	0.0058 (11)
C8	0.0350 (10)	0.0448 (12)	0.0361 (13)	−0.0052 (8)	0.0049 (9)	0.0061 (10)
C9	0.0410 (11)	0.0499 (12)	0.0323 (13)	−0.0087 (9)	0.0096 (10)	0.0051 (10)
C10	0.0358 (10)	0.0409 (11)	0.0351 (13)	−0.0031 (8)	0.0035 (9)	0.0005 (10)
C11	0.0344 (10)	0.0412 (11)	0.0359 (13)	0.0003 (8)	0.0082 (9)	0.0017 (9)
C12	0.0442 (12)	0.0561 (13)	0.0319 (13)	−0.0037 (9)	0.0095 (10)	0.0047 (10)
C13	0.0376 (11)	0.0578 (13)	0.0345 (13)	−0.0071 (9)	−0.0001 (10)	0.0023 (11)
C14	0.0398 (11)	0.0458 (12)	0.0407 (14)	−0.0005 (9)	0.0135 (10)	0.0046 (10)
C15	0.0383 (11)	0.0431 (12)	0.0418 (15)	−0.0002 (8)	0.0087 (10)	0.0048 (10)
C16	0.0374 (10)	0.0377 (11)	0.0421 (14)	0.0013 (8)	0.0091 (10)	0.0038 (10)
C17	0.0484 (13)	0.0608 (14)	0.0415 (15)	−0.0074 (10)	0.0078 (11)	0.0054 (12)
C18	0.0439 (13)	0.0612 (15)	0.0518 (17)	−0.0110 (10)	−0.0003 (12)	0.0038 (12)
C19	0.0371 (11)	0.0424 (12)	0.0585 (17)	−0.0011 (9)	0.0125 (11)	0.0057 (11)
C20	0.0502 (14)	0.0867 (18)	0.0447 (17)	−0.0078 (12)	0.0162 (13)	0.0039 (14)
C21	0.0411 (12)	0.0855 (18)	0.0430 (16)	−0.0138 (11)	0.0081 (11)	−0.0016 (13)
C22	0.0493 (15)	0.0691 (17)	0.083 (3)	0.0012 (12)	0.0110 (16)	0.0108 (18)
C23	0.091 (2)	0.169 (4)	0.060 (2)	0.023 (2)	0.0116 (19)	−0.025 (2)
C24	0.099 (3)	0.071 (2)	0.177 (5)	−0.0164 (18)	0.041 (3)	0.016 (2)

O1—C8	1.362 (2)	C8—C9	1.371 (3)
O1—C7	1.426 (3)	C8—C13	1.392 (3)
O2—C10	1.341 (3)	C9—C10	1.389 (3)
O2—H2O	0.847 (10)	C9—H9	0.9300
O3—C15	1.217 (3)	C10—C11	1.403 (3)
O4—N3	1.205 (3)	C11—C12	1.388 (3)
O5—N3	1.211 (3)	C11—C14	1.446 (3)
O6—C22	1.201 (4)	C12—C13	1.369 (3)
N1—C14	1.271 (3)	C12—H12	0.9300
N1—N2	1.374 (2)	C13—H13	0.9300
N2—C15	1.337 (3)	C14—H14	0.9300
N2—H2'	0.879 (10)	C15—C16	1.493 (3)
N3—C19	1.472 (3)	C16—C17	1.370 (3)
N4—C22	1.308 (4)	C16—C21	1.375 (3)
N4—C24	1.417 (4)	C17—C18	1.376 (3)
N4—C23	1.439 (4)	C17—H17	0.9300
C1—C2	1.371 (3)	C18—C19	1.367 (3)
C1—C6	1.379 (3)	C18—H18	0.9300
C1—H1	0.9300	C19—C20	1.354 (4)
C2—C3	1.369 (4)	C20—C21	1.380 (3)
C2—H2A	0.9300	C20—H20	0.9300
C3—C4	1.363 (3)	C21—H21	0.9300
C3—H3	0.9300	C22—H22	0.9300
C4—C5	1.383 (3)	C23—H23A	0.9600
C4—H4	0.9300	C23—H23B	0.9600
C5—C6	1.370 (3)	C23—H23C	0.9600
C5—H5	0.9300	C24—H24A	0.9600
C6—C7	1.495 (3)	C24—H24B	0.9600
C7—H7A	0.9700	C24—H24C	0.9600
C7—H7B	0.9700
C8—O1—C7	118.47 (17)	C10—C11—C14	121.7 (2)
C10—O2—H2O	107 (2)	C13—C12—C11	122.0 (2)
C14—N1—N2	118.4 (2)	C13—C12—H12	119.0
C15—N2—N1	117.33 (19)	C11—C12—H12	119.0
C15—N2—H2'	122.7 (14)	C12—C13—C8	119.1 (2)
N1—N2—H2'	119.9 (14)	C12—C13—H13	120.5
O4—N3—O5	123.4 (2)	C8—C13—H13	120.5
O4—N3—C19	118.2 (2)	N1—C14—C11	120.1 (2)
O5—N3—C19	118.4 (2)	N1—C14—H14	119.9
C22—N4—C24	121.8 (3)	C11—C14—H14	119.9
C22—N4—C23	119.5 (3)	O3—C15—N2	122.03 (19)
C24—N4—C23	118.6 (3)	O3—C15—C16	120.9 (2)
C2—C1—C6	120.3 (2)	N2—C15—C16	117.0 (2)
C2—C1—H1	119.9	C17—C16—C21	118.9 (2)
C6—C1—H1	119.9	C17—C16—C15	117.3 (2)
C3—C2—C1	120.6 (2)	C21—C16—C15	123.7 (2)
C3—C2—H2A	119.7	C16—C17—C18	121.3 (2)
C1—C2—H2A	119.7	C16—C17—H17	119.3
C4—C3—C2	119.8 (2)	C18—C17—H17	119.3
C4—C3—H3	120.1	C19—C18—C17	118.0 (2)
C2—C3—H3	120.1	C19—C18—H18	121.0
C3—C4—C5	119.6 (2)	C17—C18—H18	121.0
C3—C4—H4	120.2	C20—C19—C18	122.4 (2)
C5—C4—H4	120.2	C20—C19—N3	118.5 (2)
C6—C5—C4	121.0 (2)	C18—C19—N3	119.1 (2)
C6—C5—H5	119.5	C19—C20—C21	118.7 (2)
C4—C5—H5	119.5	C19—C20—H20	120.6
C5—C6—C1	118.66 (19)	C21—C20—H20	120.6
C5—C6—C7	121.5 (2)	C16—C21—C20	120.6 (2)
C1—C6—C7	119.9 (2)	C16—C21—H21	119.7
O1—C7—C6	108.03 (18)	C20—C21—H21	119.7
O1—C7—H7A	110.1	O6—C22—N4	125.5 (3)
C6—C7—H7A	110.1	O6—C22—H22	117.3
O1—C7—H7B	110.1	N4—C22—H22	117.3
C6—C7—H7B	110.1	N4—C23—H23A	109.5
H7A—C7—H7B	108.4	N4—C23—H23B	109.5
O1—C8—C9	124.2 (2)	H23A—C23—H23B	109.5
O1—C8—C13	114.98 (19)	N4—C23—H23C	109.5
C9—C8—C13	120.79 (19)	H23A—C23—H23C	109.5
C8—C9—C10	119.7 (2)	H23B—C23—H23C	109.5
C8—C9—H9	120.2	N4—C24—H24A	109.5
C10—C9—H9	120.2	N4—C24—H24B	109.5
O2—C10—C9	117.4 (2)	H24A—C24—H24B	109.5
O2—C10—C11	122.09 (18)	N4—C24—H24C	109.5
C9—C10—C11	120.6 (2)	H24A—C24—H24C	109.5
C12—C11—C10	117.91 (18)	H24B—C24—H24C	109.5
C12—C11—C14	120.3 (2)
C14—N1—N2—C15	−176.17 (19)	C9—C8—C13—C12	−0.1 (3)
C6—C1—C2—C3	0.3 (4)	N2—N1—C14—C11	177.93 (18)
C1—C2—C3—C4	−0.2 (4)	C12—C11—C14—N1	−176.3 (2)
C2—C3—C4—C5	0.6 (4)	C10—C11—C14—N1	3.1 (3)
C3—C4—C5—C6	−1.1 (4)	N1—N2—C15—O3	0.0 (3)
C4—C5—C6—C1	1.2 (4)	N1—N2—C15—C16	179.57 (17)
C4—C5—C6—C7	−177.5 (2)	O3—C15—C16—C17	−10.9 (3)
C2—C1—C6—C5	−0.8 (4)	N2—C15—C16—C17	169.57 (19)
C2—C1—C6—C7	177.9 (2)	O3—C15—C16—C21	166.3 (2)
C8—O1—C7—C6	−171.59 (18)	N2—C15—C16—C21	−13.2 (3)
C5—C6—C7—O1	−115.3 (2)	C21—C16—C17—C18	1.8 (4)
C1—C6—C7—O1	66.1 (3)	C15—C16—C17—C18	179.2 (2)
C7—O1—C8—C9	−0.8 (3)	C16—C17—C18—C19	−0.1 (4)
C7—O1—C8—C13	178.96 (19)	C17—C18—C19—C20	−1.4 (4)
O1—C8—C9—C10	179.29 (19)	C17—C18—C19—N3	179.2 (2)
C13—C8—C9—C10	−0.4 (3)	O4—N3—C19—C20	−176.6 (3)
C8—C9—C10—O2	179.93 (19)	O5—N3—C19—C20	4.3 (3)
C8—C9—C10—C11	0.4 (3)	O4—N3—C19—C18	2.7 (3)
O2—C10—C11—C12	−179.36 (19)	O5—N3—C19—C18	−176.4 (2)
C9—C10—C11—C12	0.1 (3)	C18—C19—C20—C21	1.2 (4)
O2—C10—C11—C14	1.3 (3)	N3—C19—C20—C21	−179.5 (2)
C9—C10—C11—C14	−179.25 (19)	C17—C16—C21—C20	−2.1 (4)
C10—C11—C12—C13	−0.7 (3)	C15—C16—C21—C20	−179.3 (2)
C14—C11—C12—C13	178.7 (2)	C19—C20—C21—C16	0.6 (4)
C11—C12—C13—C8	0.7 (3)	C24—N4—C22—O6	−0.9 (4)
O1—C8—C13—C12	−179.87 (19)	C23—N4—C22—O6	−178.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2′···O6	0.88 (1)	1.95 (1)	2.810 (3)	166 (2)
O2—H2O···N1	0.85 (1)	1.82 (2)	2.583 (2)	149 (3)
C7—H7B···O3i	0.97	2.49	3.167 (3)	127
C13—H13···O1ii	0.93	2.58	3.448 (3)	156
C21—H21···O6	0.93	2.42	3.206 (3)	143
C12—H12···Cg1ii	0.93	2.91	3.673 (2)	140
C17—H17···Cg1i	0.93	2.85	3.630 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2′⋯O6	0.88 (1)	1.95 (1)	2.810 (3)	166 (2)
O2—H2O⋯N1	0.85 (1)	1.82 (2)	2.583 (2)	149 (3)
C7—H7B⋯O3i	0.97	2.49	3.167 (3)	127
C13—H13⋯O1ii	0.93	2.58	3.448 (3)	156
C21—H21⋯O6	0.93	2.42	3.206 (3)	143
C12—H12⋯Cg1ii	0.93	2.91	3.673 (2)	140
C17—H17⋯Cg1i	0.93	2.85	3.630 (3)	142

Symmetry codes: (i) ; (ii) .