tert-Butyl N-{[5-(5-oxohexa-namido)-pyridin-2-yl]amino}-carbamate.

In the crystal structure of the title compound, C16H24N4O4, mol-ecules are linked by N-H⋯O hydrogen bonds between the carbonyl groups of the carbamoyl and amido functional groups and the amino groups, and by N-H⋯N hydrogen bonds between the amino group and the pyridine ring, forming two-dimensional networks parallel to the ab plane.

Related literature

For the synthesis, properties and biological activity of 2-hydrazino­pyridine derivatives, see: Ardisson et al. (2005 ▶); Jurisson & Lydon (1999 ▶); Abrams et al. (1994 ▶); Liu et al. (2011 ▶); Lu et al. (2011 ▶); Schwartz et al. (1990 ▶). For the crystal structures of related compounds, see: Banerjee et al. (2005 ▶); Rose et al. (1998 ▶); Zora et al. (2006 ▶). For synthesis, see: Cugola et al. (1995 ▶).

Experimental

Crystal data

C16H24N4O4

M = 336.39

Triclinic,

a = 6.2598 (4) Å

b = 9.2822 (6) Å

c = 16.0437 (12) Å

α = 84.387 (6)°

β = 88.957 (6)°

γ = 79.358 (6)°

V = 911.79 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.84 × 0.17 × 0.06 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.928, T max = 0.994

20299 measured reflections

3295 independent reflections

2187 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.147

S = 1.04

3295 reflections

221 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.25 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DIRAX/LSQ (Duisenberg, 1992 ▶); data reduction: EVALCCD (Duisenberg et al., 2003 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813024598/ff2115sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813024598/ff2115Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813024598/ff2115Isup3.cml

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

C16H24N4O4	Z = 2
Mr = 336.39	F(000) = 360
Triclinic, P1	Dx = 1.225 Mg m−3
a = 6.2598 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.2822 (6) Å	Cell parameters from 8003 reflections
c = 16.0437 (12) Å	θ = 3.2–25.3°
α = 84.387 (6)°	µ = 0.09 mm−1
β = 88.957 (6)°	T = 293 K
γ = 79.358 (6)°	Plate, colourless
V = 911.79 (11) Å3	0.84 × 0.17 × 0.06 mm

Bruker–Nonius KappaCCD diffractometer	2187 reflections with I > 2σ(I)
intensities from φ scan and ω scan	Rint = 0.038
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	θmax = 25.3°, θmin = 3.2°
Tmin = 0.928, Tmax = 0.994	h = −7→7
20299 measured reflections	k = −11→11
3295 independent reflections	l = −19→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053	H-atom parameters constrained
wR(F2) = 0.147	w = 1/[σ2(Fo2) + (0.061P)2 + 0.4578P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3295 reflections	Δρmax = 0.29 e Å−3
221 parameters	Δρmin = −0.25 e Å−3
0 restraints

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.

	x	y	z	Uiso*/Ueq
N2	0.2722 (3)	0.91380 (18)	0.96382 (11)	0.0383 (4)
N1	0.8167 (3)	0.79747 (19)	0.88090 (12)	0.0420 (5)
H1	0.8436	0.8828	0.8633	0.050*
C8	0.6222 (4)	0.6875 (2)	0.99807 (14)	0.0452 (6)
H8	0.7405	0.6120	1.0105	0.054*
N3	0.0661 (3)	0.8185 (2)	1.06579 (12)	0.0480 (5)
H3	−0.0492	0.8704	1.0424	0.058*
O4	0.0851 (3)	0.71283 (17)	1.28015 (10)	0.0579 (5)
C10	0.2624 (3)	0.8083 (2)	1.02536 (13)	0.0376 (5)
C11	0.4549 (3)	0.9045 (2)	0.91869 (13)	0.0388 (5)
H11	0.4618	0.9774	0.8752	0.047*
O2	0.9342 (3)	0.55429 (18)	0.87934 (12)	0.0663 (5)
N4	0.0544 (3)	0.7449 (2)	1.14426 (12)	0.0476 (5)
H4	0.0149	0.6605	1.1495	0.057*
C7	0.6329 (3)	0.7943 (2)	0.93254 (13)	0.0369 (5)
O3	0.1590 (3)	0.92288 (18)	1.21135 (11)	0.0640 (5)
C6	0.9535 (4)	0.6804 (2)	0.85656 (14)	0.0439 (6)
C9	0.4362 (4)	0.6941 (2)	1.04441 (14)	0.0462 (6)
H9	0.4260	0.6226	1.0884	0.055*
C12	0.1045 (4)	0.8044 (2)	1.21198 (15)	0.0461 (6)
C5	1.1308 (4)	0.7170 (3)	0.79916 (18)	0.0620 (7)
H5A	1.0644	0.7759	0.7499	0.074*
H5B	1.2121	0.7776	0.8272	0.074*
C2	1.4473 (6)	0.7179 (4)	0.6461 (2)	0.0740 (8)
C13	0.1179 (5)	0.7546 (3)	1.36427 (16)	0.0663 (8)
C4	1.2840 (5)	0.5918 (4)	0.7717 (2)	0.0931 (12)
H4A	1.2109	0.5423	0.7334	0.112*
H4B	1.3307	0.5222	0.8199	0.112*
O1	1.2875 (5)	0.7200 (4)	0.60720 (16)	0.1353 (12)
C15	−0.0383 (7)	0.8914 (4)	1.3805 (2)	0.1030 (13)
H15A	0.0014	0.9742	1.3473	0.154*
H15B	−0.0341	0.9063	1.4388	0.154*
H15C	−0.1825	0.8815	1.3658	0.154*
C3	1.4820 (5)	0.6376 (5)	0.7287 (2)	0.1002 (13)
H3A	1.5420	0.6983	0.7646	0.120*
H3B	1.5906	0.5497	0.7237	0.120*
C1	1.6198 (8)	0.7953 (5)	0.6113 (3)	0.1350 (18)
H1A	1.6100	0.8071	0.5513	0.203*
H1B	1.7593	0.7387	0.6279	0.203*
H1C	1.6022	0.8903	0.6321	0.203*
C16	0.0675 (7)	0.6234 (4)	1.41952 (19)	0.0943 (11)
H16A	−0.0786	0.6116	1.4092	0.142*
H16B	0.0821	0.6391	1.4772	0.142*
H16C	0.1669	0.5363	1.4072	0.142*
C14	0.3522 (7)	0.7691 (5)	1.3740 (2)	0.1111 (13)
H14A	0.4454	0.6793	1.3617	0.167*
H14B	0.3770	0.7881	1.4304	0.167*
H14C	0.3832	0.8491	1.3359	0.167*

	U11	U22	U33	U12	U13	U23
N2	0.0429 (11)	0.0323 (10)	0.0384 (10)	−0.0052 (8)	0.0023 (8)	−0.0001 (8)
N1	0.0428 (11)	0.0303 (10)	0.0531 (12)	−0.0092 (8)	0.0086 (9)	−0.0018 (8)
C8	0.0449 (14)	0.0346 (12)	0.0516 (14)	0.0005 (10)	0.0001 (11)	0.0037 (10)
N3	0.0438 (12)	0.0504 (12)	0.0432 (11)	−0.0003 (9)	0.0058 (9)	0.0115 (9)
O4	0.0911 (13)	0.0425 (10)	0.0428 (10)	−0.0241 (9)	0.0090 (8)	0.0042 (7)
C10	0.0424 (13)	0.0334 (12)	0.0373 (12)	−0.0090 (9)	0.0000 (9)	−0.0020 (9)
C11	0.0465 (14)	0.0312 (12)	0.0383 (12)	−0.0090 (10)	0.0011 (10)	0.0016 (9)
O2	0.0826 (13)	0.0343 (10)	0.0792 (13)	−0.0052 (9)	0.0231 (10)	−0.0060 (9)
N4	0.0630 (13)	0.0354 (10)	0.0437 (11)	−0.0130 (9)	0.0095 (9)	0.0049 (9)
C7	0.0384 (12)	0.0313 (11)	0.0424 (12)	−0.0096 (9)	0.0017 (9)	−0.0046 (9)
O3	0.0948 (14)	0.0404 (10)	0.0608 (11)	−0.0279 (9)	0.0081 (10)	0.0031 (8)
C6	0.0468 (14)	0.0367 (13)	0.0488 (14)	−0.0076 (10)	0.0007 (10)	−0.0077 (10)
C9	0.0507 (14)	0.0358 (13)	0.0471 (13)	−0.0022 (10)	0.0045 (11)	0.0100 (10)
C12	0.0535 (15)	0.0349 (13)	0.0479 (14)	−0.0088 (11)	0.0110 (11)	0.0050 (11)
C5	0.0559 (16)	0.0620 (17)	0.0733 (18)	−0.0168 (13)	0.0195 (13)	−0.0244 (14)
C2	0.073 (2)	0.089 (2)	0.0620 (19)	−0.0139 (17)	0.0123 (17)	−0.0204 (17)
C13	0.096 (2)	0.0598 (18)	0.0455 (15)	−0.0248 (15)	0.0073 (14)	0.0013 (13)
C4	0.089 (2)	0.079 (2)	0.087 (2)	0.0318 (18)	0.0401 (19)	0.0168 (18)
O1	0.112 (2)	0.239 (4)	0.0606 (16)	−0.050 (2)	−0.0055 (15)	−0.0106 (19)
C15	0.154 (4)	0.075 (2)	0.080 (2)	−0.018 (2)	0.038 (2)	−0.0189 (18)
C3	0.063 (2)	0.147 (3)	0.071 (2)	0.027 (2)	0.0151 (16)	0.000 (2)
C1	0.126 (4)	0.117 (4)	0.169 (5)	−0.046 (3)	0.046 (3)	−0.009 (3)
C16	0.156 (3)	0.077 (2)	0.0518 (18)	−0.037 (2)	0.0132 (19)	0.0112 (16)
C14	0.122 (3)	0.133 (4)	0.086 (3)	−0.050 (3)	−0.025 (2)	0.011 (2)

N2—C10	1.330 (3)	C5—C4	1.462 (4)
N2—C11	1.336 (3)	C2—O1	1.185 (4)
N1—H1	0.8600	C2—C3	1.454 (4)
N1—C7	1.409 (3)	C2—C1	1.476 (5)
N1—C6	1.339 (3)	C13—C15	1.494 (4)
C8—H8	0.9300	C13—C16	1.513 (4)
C8—C7	1.382 (3)	C13—C14	1.510 (5)
C8—C9	1.365 (3)	C4—H4A	0.9700
N3—H3	0.8600	C4—H4B	0.9700
N3—C10	1.372 (3)	C4—C3	1.517 (4)
N3—N4	1.380 (2)	C15—H15A	0.9600
O4—C12	1.336 (3)	C15—H15B	0.9600
O4—C13	1.468 (3)	C15—H15C	0.9600
C10—C9	1.386 (3)	C3—H3A	0.9700
C11—H11	0.9300	C3—H3B	0.9700
C11—C7	1.372 (3)	C1—H1A	0.9600
O2—C6	1.219 (3)	C1—H1B	0.9600
N4—H4	0.8600	C1—H1C	0.9600
N4—C12	1.333 (3)	C16—H16A	0.9600
O3—C12	1.209 (3)	C16—H16B	0.9600
C6—C5	1.495 (3)	C16—H16C	0.9600
C9—H9	0.9300	C14—H14A	0.9600
C5—H5A	0.9700	C14—H14B	0.9600
C5—H5B	0.9700	C14—H14C	0.9600
C10—N2—C11	117.63 (18)	O4—C13—C16	101.9 (2)
C7—N1—H1	116.9	O4—C13—C14	109.3 (3)
C6—N1—H1	116.9	C15—C13—C16	110.7 (3)
C6—N1—C7	126.27 (18)	C15—C13—C14	112.9 (3)
C7—C8—H8	120.4	C14—C13—C16	110.8 (3)
C9—C8—H8	120.4	C5—C4—H4A	109.1
C9—C8—C7	119.3 (2)	C5—C4—H4B	109.1
C10—N3—H3	120.2	C5—C4—C3	112.4 (3)
C10—N3—N4	119.59 (18)	H4A—C4—H4B	107.8
N4—N3—H3	120.2	C3—C4—H4A	109.1
C12—O4—C13	121.02 (19)	C3—C4—H4B	109.1
N2—C10—N3	114.92 (18)	C13—C15—H15A	109.5
N2—C10—C9	122.0 (2)	C13—C15—H15B	109.5
N3—C10—C9	123.07 (19)	C13—C15—H15C	109.5
N2—C11—H11	117.9	H15A—C15—H15B	109.5
N2—C11—C7	124.12 (19)	H15A—C15—H15C	109.5
C7—C11—H11	117.9	H15B—C15—H15C	109.5
N3—N4—H4	120.0	C2—C3—C4	116.5 (3)
C12—N4—N3	120.07 (19)	C2—C3—H3A	108.2
C12—N4—H4	120.0	C2—C3—H3B	108.2
C8—C7—N1	123.77 (19)	C4—C3—H3A	108.2
C11—C7—N1	118.68 (19)	C4—C3—H3B	108.2
C11—C7—C8	117.5 (2)	H3A—C3—H3B	107.3
N1—C6—C5	114.7 (2)	C2—C1—H1A	109.5
O2—C6—N1	122.5 (2)	C2—C1—H1B	109.5
O2—C6—C5	122.8 (2)	C2—C1—H1C	109.5
C8—C9—C10	119.5 (2)	H1A—C1—H1B	109.5
C8—C9—H9	120.3	H1A—C1—H1C	109.5
C10—C9—H9	120.3	H1B—C1—H1C	109.5
N4—C12—O4	109.39 (19)	C13—C16—H16A	109.5
O3—C12—O4	125.6 (2)	C13—C16—H16B	109.5
O3—C12—N4	125.0 (2)	C13—C16—H16C	109.5
C6—C5—H5A	108.3	H16A—C16—H16B	109.5
C6—C5—H5B	108.3	H16A—C16—H16C	109.5
H5A—C5—H5B	107.4	H16B—C16—H16C	109.5
C4—C5—C6	116.1 (2)	C13—C14—H14A	109.5
C4—C5—H5A	108.3	C13—C14—H14B	109.5
C4—C5—H5B	108.3	C13—C14—H14C	109.5
O1—C2—C3	121.4 (3)	H14A—C14—H14B	109.5
O1—C2—C1	120.7 (4)	H14A—C14—H14C	109.5
C3—C2—C1	117.8 (4)	H14B—C14—H14C	109.5
O4—C13—C15	110.7 (3)
N2—C10—C9—C8	−1.1 (3)	C7—N1—C6—C5	178.0 (2)
N2—C11—C7—N1	−179.53 (19)	C7—C8—C9—C10	−0.6 (4)
N2—C11—C7—C8	−0.9 (3)	C6—N1—C7—C8	34.9 (3)
N1—C6—C5—C4	179.6 (3)	C6—N1—C7—C11	−146.5 (2)
N3—C10—C9—C8	176.3 (2)	C6—C5—C4—C3	−168.4 (3)
N3—N4—C12—O4	−178.94 (18)	C9—C8—C7—N1	−179.9 (2)
N3—N4—C12—O3	1.0 (4)	C9—C8—C7—C11	1.5 (3)
C10—N2—C11—C7	−0.7 (3)	C12—O4—C13—C15	59.1 (3)
C10—N3—N4—C12	82.6 (3)	C12—O4—C13—C16	176.9 (2)
C11—N2—C10—N3	−175.89 (18)	C12—O4—C13—C14	−65.8 (3)
C11—N2—C10—C9	1.7 (3)	C5—C4—C3—C2	−70.8 (4)
O2—C6—C5—C4	−0.5 (4)	C13—O4—C12—N4	−176.3 (2)
N4—N3—C10—N2	−160.78 (19)	C13—O4—C12—O3	3.8 (4)
N4—N3—C10—C9	21.6 (3)	O1—C2—C3—C4	−15.7 (5)
C7—N1—C6—O2	−1.8 (4)	C1—C2—C3—C4	165.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.86	2.06	2.888 (2)	161
N3—H3···N2ii	0.86	2.21	2.957 (3)	145
N4—H4···O2iii	0.86	2.06	2.827 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.86	2.06	2.888 (2)	161
N3—H3⋯N2ii	0.86	2.21	2.957 (3)	145
N4—H4⋯O2iii	0.86	2.06	2.827 (3)	149

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