N,N-Bis(2,2-dimethyl-propano-yl)benzene-1,3-dicarbohydrazide.

In the mol-ecular structure of the title hydrazide derivative, C(18)H(26)N(4)O(4), the conformations of the two units of 2-(2,2-dimethyl-1-oxoprop-yl)hydrazide substituents are not planar; these two units are attached axially to the benzene ring with C(ortho)-C-C(=O)-N torsion angles of 28.1 (2) and 31.0 (2)° [where C(ortho) is the C atom at position 4 of the benzene ring relative to the substituent at position 3 or the C atom at position 6 of the benzene ring relative to the substituent at position 1, as appropriate]. The dihedral angles between the hydrazide units and the benzene ring are 62.66 (7) and 63.84 (7)°. In the crystal structure, mol-ecules are arranged in an anti-parallel manner and are linked by N-H⋯O inter-molecular hydrogen bonds and weak C-H⋯O inter-molecular inter-actions into a three-dimensional network. The structure is further stabilized by a weak C-H⋯N intra-molecular inter-action.

Related literature

For values of bond lengths, see: Allen et al. (1987 ▶). For related literature on the applications and bioactivities of hydrazide derivatives, see for example: Feng et al. (2006 ▶); Fernández et al. (2004 ▶); Hołtra et al. (2007 ▶); Imramovský et al. (2007 ▶); Kim et al. (2007 ▶); Lemay et al. (2007 ▶); Liu et al. (2006 ▶); Nica et al. (2007 ▶); Raveendran & Pal (2007 ▶); Rivero & Buchwald (2007 ▶); Sicardi et al. (1980 ▶); Yang et al. (2007 ▶).

Experimental

Crystal data

C18H26N4O4

M = 362.43

Monoclinic,

a = 7.1853 (2) Å

b = 14.8928 (4) Å

c = 17.1656 (5) Å

β = 96.050 (2)°

V = 1826.65 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100.0 (1) K

0.56 × 0.10 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.949, T max = 0.993

34290 measured reflections

5301 independent reflections

3858 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.141

S = 1.06

5301 reflections

257 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 1998 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807063210/is2255sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063210/is2255Isup2.hkl

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

C18H26N4O4	F000 = 776
Mr = 362.43	Dx = 1.318 Mg m−3
Monoclinic, P21/c	Melting point: over 523 K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 7.1853 (2) Å	Cell parameters from 5301 reflections
b = 14.8928 (4) Å	θ = 2.4–30.0º
c = 17.1656 (5) Å	µ = 0.10 mm−1
β = 96.050 (2)º	T = 100.0 (1) K
V = 1826.65 (9) Å3	Needle, colorless
Z = 4	0.56 × 0.10 × 0.08 mm

Bruker SMART APEXII CCD area-detector diffractometer	5301 independent reflections
Radiation source: fine-focus sealed tube	3858 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.071
Detector resolution: 8.33 pixels mm-1	θmax = 30.0º
T = 100.0(1) K	θmin = 2.4º
ω scans	h = −10→10
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −20→20
Tmin = 0.949, Tmax = 0.993	l = −24→24
34290 measured reflections

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)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.141	w = 1/[σ2(Fo2) + (0.0619P)2 + 0.4134P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
5301 reflections	Δρmax = 0.46 e Å−3
257 parameters	Δρmin = −0.28 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	0.60769 (16)	0.05613 (7)	0.25206 (6)	0.0237 (3)
O2	0.38220 (15)	0.21786 (7)	0.36444 (6)	0.0184 (2)
O3	0.11704 (15)	0.22624 (7)	0.62797 (6)	0.0187 (2)
O4	−0.10708 (16)	0.07187 (7)	0.73429 (6)	0.0240 (3)
N1	0.33903 (19)	0.13157 (8)	0.22251 (7)	0.0184 (3)
N2	0.27315 (19)	0.09916 (9)	0.29066 (7)	0.0184 (3)
N3	0.23552 (18)	0.11418 (8)	0.70784 (7)	0.0172 (3)
N4	0.15571 (19)	0.14796 (8)	0.77239 (7)	0.0173 (3)
C1	0.2816 (2)	−0.00484 (9)	0.43413 (8)	0.0159 (3)
H1A	0.3021	−0.0379	0.3899	0.019*
C2	0.2495 (2)	−0.04858 (9)	0.50312 (8)	0.0171 (3)
H2A	0.2474	−0.1110	0.5046	0.021*
C3	0.2207 (2)	0.00018 (9)	0.56966 (8)	0.0157 (3)
H3A	0.1998	−0.0295	0.6156	0.019*
C4	0.2231 (2)	0.09396 (9)	0.56759 (7)	0.0142 (3)
C5	0.25445 (19)	0.13769 (9)	0.49847 (7)	0.0150 (3)
H5A	0.2563	0.2001	0.4969	0.018*
C6	0.2831 (2)	0.08878 (9)	0.43155 (7)	0.0143 (3)
C7	0.3208 (2)	0.14076 (9)	0.36016 (8)	0.0152 (3)
C8	0.5108 (2)	0.10397 (9)	0.20601 (8)	0.0177 (3)
C9	0.5743 (2)	0.13472 (10)	0.12760 (9)	0.0219 (3)
C10	0.7443 (3)	0.07870 (14)	0.11231 (11)	0.0404 (5)
H10A	0.8442	0.0897	0.1529	0.061*
H10B	0.7840	0.0950	0.0625	0.061*
H10C	0.7118	0.0162	0.1119	0.061*
C11	0.6266 (3)	0.23490 (11)	0.13166 (10)	0.0281 (4)
H11A	0.7375	0.2430	0.1673	0.042*
H11B	0.5257	0.2687	0.1496	0.042*
H11C	0.6494	0.2555	0.0805	0.042*
C12	0.4177 (3)	0.11974 (11)	0.06080 (9)	0.0270 (4)
H12A	0.3870	0.0570	0.0573	0.040*
H12B	0.4593	0.1394	0.0123	0.040*
H12C	0.3090	0.1534	0.0711	0.040*
C13	0.1843 (2)	0.15065 (9)	0.63621 (8)	0.0151 (3)
C14	−0.0226 (2)	0.12316 (9)	0.78142 (8)	0.0166 (3)
C15	−0.1087 (2)	0.16126 (10)	0.85232 (8)	0.0185 (3)
C16	−0.2991 (3)	0.11803 (12)	0.85580 (10)	0.0298 (4)
H16A	−0.2844	0.0542	0.8613	0.045*
H16B	−0.3778	0.1312	0.8085	0.045*
H16C	−0.3554	0.1414	0.8999	0.045*
C17	−0.1340 (2)	0.26337 (10)	0.84314 (9)	0.0242 (3)
H17A	−0.2175	0.2759	0.7970	0.036*
H17B	−0.0148	0.2908	0.8384	0.036*
H17C	−0.1853	0.2871	0.8883	0.036*
C18	0.0197 (2)	0.14110 (12)	0.92760 (8)	0.0259 (4)
H18A	0.0268	0.0774	0.9357	0.039*
H18B	−0.0301	0.1690	0.9714	0.039*
H18C	0.1426	0.1643	0.9228	0.039*
H1N1	0.269 (3)	0.1724 (13)	0.1938 (11)	0.032 (5)*
H1N2	0.235 (3)	0.0455 (12)	0.2878 (10)	0.019 (4)*
H1N3	0.276 (3)	0.0588 (12)	0.7132 (10)	0.023 (5)*
H1N4	0.215 (3)	0.1885 (12)	0.8028 (11)	0.025 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0249 (6)	0.0224 (5)	0.0232 (5)	0.0051 (4)	−0.0001 (5)	0.0054 (4)
O2	0.0197 (6)	0.0175 (5)	0.0182 (5)	−0.0023 (4)	0.0031 (4)	0.0015 (4)
O3	0.0208 (6)	0.0174 (5)	0.0184 (5)	0.0020 (4)	0.0041 (4)	0.0004 (4)
O4	0.0255 (6)	0.0245 (5)	0.0217 (5)	−0.0061 (5)	0.0013 (5)	−0.0053 (4)
N1	0.0213 (7)	0.0212 (6)	0.0133 (5)	0.0034 (5)	0.0050 (5)	0.0042 (5)
N2	0.0246 (7)	0.0188 (6)	0.0127 (5)	−0.0039 (5)	0.0057 (5)	0.0006 (4)
N3	0.0217 (7)	0.0184 (6)	0.0123 (5)	0.0038 (5)	0.0049 (5)	−0.0008 (4)
N4	0.0192 (7)	0.0203 (6)	0.0131 (5)	−0.0009 (5)	0.0050 (5)	−0.0044 (4)
C1	0.0166 (7)	0.0180 (6)	0.0133 (6)	0.0001 (5)	0.0024 (5)	−0.0026 (5)
C2	0.0183 (7)	0.0148 (6)	0.0183 (6)	−0.0005 (5)	0.0020 (5)	0.0001 (5)
C3	0.0157 (7)	0.0176 (6)	0.0139 (6)	−0.0008 (5)	0.0021 (5)	0.0008 (5)
C4	0.0113 (7)	0.0180 (6)	0.0132 (6)	0.0003 (5)	0.0012 (5)	−0.0015 (5)
C5	0.0142 (7)	0.0151 (6)	0.0155 (6)	−0.0009 (5)	0.0015 (5)	−0.0002 (5)
C6	0.0116 (7)	0.0177 (6)	0.0133 (6)	−0.0011 (5)	0.0005 (5)	0.0006 (5)
C7	0.0123 (7)	0.0179 (6)	0.0157 (6)	0.0018 (5)	0.0025 (5)	0.0008 (5)
C8	0.0215 (8)	0.0157 (6)	0.0160 (6)	−0.0003 (5)	0.0024 (5)	−0.0004 (5)
C9	0.0231 (8)	0.0247 (7)	0.0192 (7)	0.0043 (6)	0.0078 (6)	0.0055 (6)
C10	0.0371 (12)	0.0497 (11)	0.0387 (10)	0.0206 (9)	0.0236 (9)	0.0158 (9)
C11	0.0261 (9)	0.0297 (8)	0.0287 (8)	−0.0028 (7)	0.0037 (7)	0.0079 (7)
C12	0.0373 (10)	0.0286 (8)	0.0157 (7)	−0.0005 (7)	0.0059 (6)	0.0005 (6)
C13	0.0126 (7)	0.0172 (6)	0.0158 (6)	−0.0019 (5)	0.0026 (5)	−0.0003 (5)
C14	0.0197 (8)	0.0153 (6)	0.0148 (6)	−0.0008 (5)	0.0028 (5)	0.0010 (5)
C15	0.0183 (8)	0.0201 (7)	0.0180 (6)	−0.0006 (6)	0.0061 (5)	−0.0014 (5)
C16	0.0243 (9)	0.0319 (9)	0.0350 (9)	−0.0069 (7)	0.0121 (7)	−0.0048 (7)
C17	0.0245 (9)	0.0225 (7)	0.0265 (7)	0.0012 (6)	0.0067 (6)	−0.0031 (6)
C18	0.0290 (9)	0.0340 (9)	0.0155 (7)	0.0056 (7)	0.0057 (6)	−0.0006 (6)

O1—C8	1.2252 (17)	C8—C9	1.536 (2)
O2—C7	1.2295 (17)	C9—C10	1.525 (2)
O3—C13	1.2273 (17)	C9—C12	1.536 (2)
O4—C14	1.2261 (17)	C9—C11	1.538 (2)
N1—C8	1.359 (2)	C10—H10A	0.9600
N1—N2	1.3935 (16)	C10—H10B	0.9600
N1—H1N1	0.90 (2)	C10—H10C	0.9600
N2—C7	1.3559 (17)	C11—H11A	0.9600
N2—H1N2	0.844 (18)	C11—H11B	0.9600
N3—C13	1.3592 (17)	C11—H11C	0.9600
N3—N4	1.3942 (16)	C12—H12A	0.9600
N3—H1N3	0.876 (18)	C12—H12B	0.9600
N4—C14	1.357 (2)	C12—H12C	0.9600
N4—H1N4	0.879 (19)	C14—C15	1.5314 (19)
C1—C2	1.3920 (18)	C15—C16	1.519 (2)
C1—C6	1.3951 (19)	C15—C18	1.536 (2)
C1—H1A	0.9300	C15—C17	1.538 (2)
C2—C3	1.3874 (19)	C16—H16A	0.9600
C2—H2A	0.9300	C16—H16B	0.9600
C3—C4	1.3973 (19)	C16—H16C	0.9600
C3—H3A	0.9300	C17—H17A	0.9600
C4—C5	1.3926 (18)	C17—H17B	0.9600
C4—C13	1.4990 (19)	C17—H17C	0.9600
C5—C6	1.3937 (18)	C18—H18A	0.9600
C5—H5A	0.9300	C18—H18B	0.9600
C6—C7	1.4979 (19)	C18—H18C	0.9600
C8—N1—N2	117.82 (12)	C9—C10—H10C	109.5
C8—N1—H1N1	123.8 (13)	H10A—C10—H10C	109.5
N2—N1—H1N1	118.3 (13)	H10B—C10—H10C	109.5
C7—N2—N1	120.25 (12)	C9—C11—H11A	109.5
C7—N2—H1N2	122.2 (12)	C9—C11—H11B	109.5
N1—N2—H1N2	114.5 (12)	H11A—C11—H11B	109.5
C13—N3—N4	118.68 (12)	C9—C11—H11C	109.5
C13—N3—H1N3	121.8 (12)	H11A—C11—H11C	109.5
N4—N3—H1N3	114.6 (12)	H11B—C11—H11C	109.5
C14—N4—N3	117.68 (12)	C9—C12—H12A	109.5
C14—N4—H1N4	121.6 (12)	C9—C12—H12B	109.5
N3—N4—H1N4	120.4 (12)	H12A—C12—H12B	109.5
C2—C1—C6	119.81 (12)	C9—C12—H12C	109.5
C2—C1—H1A	120.1	H12A—C12—H12C	109.5
C6—C1—H1A	120.1	H12B—C12—H12C	109.5
C3—C2—C1	120.54 (13)	O3—C13—N3	122.45 (12)
C3—C2—H2A	119.7	O3—C13—C4	121.99 (12)
C1—C2—H2A	119.7	N3—C13—C4	115.51 (12)
C2—C3—C4	119.93 (12)	O4—C14—N4	120.13 (13)
C2—C3—H3A	120.0	O4—C14—C15	122.80 (14)
C4—C3—H3A	120.0	N4—C14—C15	117.07 (12)
C5—C4—C3	119.52 (12)	C16—C15—C14	108.38 (12)
C5—C4—C13	117.80 (12)	C16—C15—C18	110.34 (13)
C3—C4—C13	122.63 (12)	C14—C15—C18	109.82 (12)
C4—C5—C6	120.60 (13)	C16—C15—C17	109.03 (13)
C4—C5—H5A	119.7	C14—C15—C17	109.77 (12)
C6—C5—H5A	119.7	C18—C15—C17	109.48 (12)
C5—C6—C1	119.60 (12)	C15—C16—H16A	109.5
C5—C6—C7	117.34 (12)	C15—C16—H16B	109.5
C1—C6—C7	123.03 (12)	H16A—C16—H16B	109.5
O2—C7—N2	122.34 (12)	C15—C16—H16C	109.5
O2—C7—C6	121.90 (12)	H16A—C16—H16C	109.5
N2—C7—C6	115.66 (12)	H16B—C16—H16C	109.5
O1—C8—N1	120.54 (13)	C15—C17—H17A	109.5
O1—C8—C9	122.55 (14)	C15—C17—H17B	109.5
N1—C8—C9	116.91 (12)	H17A—C17—H17B	109.5
C10—C9—C12	109.22 (14)	C15—C17—H17C	109.5
C10—C9—C8	107.75 (13)	H17A—C17—H17C	109.5
C12—C9—C8	110.45 (13)	H17B—C17—H17C	109.5
C10—C9—C11	109.98 (15)	C15—C18—H18A	109.5
C12—C9—C11	109.34 (12)	C15—C18—H18B	109.5
C8—C9—C11	110.08 (12)	H18A—C18—H18B	109.5
C9—C10—H10A	109.5	C15—C18—H18C	109.5
C9—C10—H10B	109.5	H18A—C18—H18C	109.5
H10A—C10—H10B	109.5	H18B—C18—H18C	109.5
C8—N1—N2—C7	85.19 (17)	O1—C8—C9—C10	13.0 (2)
C13—N3—N4—C14	76.61 (17)	N1—C8—C9—C10	−166.35 (14)
C6—C1—C2—C3	−0.6 (2)	O1—C8—C9—C12	132.24 (15)
C1—C2—C3—C4	0.2 (2)	N1—C8—C9—C12	−47.12 (17)
C2—C3—C4—C5	0.0 (2)	O1—C8—C9—C11	−106.92 (16)
C2—C3—C4—C13	177.12 (13)	N1—C8—C9—C11	73.72 (17)
C3—C4—C5—C6	0.1 (2)	N4—N3—C13—O3	21.9 (2)
C13—C4—C5—C6	−177.15 (13)	N4—N3—C13—C4	−160.69 (12)
C4—C5—C6—C1	−0.5 (2)	C5—C4—C13—O3	25.5 (2)
C4—C5—C6—C7	−178.47 (13)	C3—C4—C13—O3	−151.62 (15)
C2—C1—C6—C5	0.7 (2)	C5—C4—C13—N3	−151.89 (13)
C2—C1—C6—C7	178.61 (13)	C3—C4—C13—N3	31.0 (2)
N1—N2—C7—O2	17.9 (2)	N3—N4—C14—O4	0.9 (2)
N1—N2—C7—C6	−165.58 (12)	N3—N4—C14—C15	−179.64 (12)
C5—C6—C7—O2	22.5 (2)	O4—C14—C15—C16	5.10 (19)
C1—C6—C7—O2	−155.42 (14)	N4—C14—C15—C16	−174.36 (13)
C5—C6—C7—N2	−154.00 (13)	O4—C14—C15—C18	125.70 (15)
C1—C6—C7—N2	28.1 (2)	N4—C14—C15—C18	−53.76 (17)
N2—N1—C8—O1	−3.9 (2)	O4—C14—C15—C17	−113.89 (16)
N2—N1—C8—C9	175.47 (12)	N4—C14—C15—C17	66.65 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O3i	0.90 (2)	2.12 (2)	3.0193 (16)	176.7 (16)
N2—H1N2···O4ii	0.845 (18)	1.993 (19)	2.8262 (17)	169 (2)
N3—H1N3···O1iii	0.876 (18)	1.969 (18)	2.8307 (16)	167.3 (16)
N4—H1N4···O2iv	0.878 (19)	2.059 (19)	2.9320 (16)	172.3 (19)
C1—H1A···O4ii	0.93	2.48	3.1879 (17)	133
C3—H3A···O1iii	0.93	2.56	3.2854 (17)	135
C12—H12C···O3i	0.96	2.52	3.433 (2)	159
C18—H18C···N4	0.96	2.61	2.9347 (19)	100

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O3i	0.90 (2)	2.12 (2)	3.0193 (16)	176.7 (16)
N2—H1N2⋯O4ii	0.845 (18)	1.993 (19)	2.8262 (17)	169 (2)
N3—H1N3⋯O1iii	0.876 (18)	1.969 (18)	2.8307 (16)	167.3 (16)
N4—H1N4⋯O2iv	0.878 (19)	2.059 (19)	2.9320 (16)	172.3 (19)
C1—H1A⋯O4ii	0.93	2.48	3.1879 (17)	133
C3—H3A⋯O1iii	0.93	2.56	3.2854 (17)	135
C12—H12C⋯O3i	0.96	2.52	3.433 (2)	159
C18—H18C⋯N4	0.96	2.61	2.9347 (19)	100

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .