Methyl 2-{6-[(1-meth-oxy-1-oxopropan-2-yl)amino-carbon-yl]pyridine-2-carboxamido}-propano-ate.

In the title compound, C(15)H(19)N(3)O(6), the amide planes are inclined at dihedral angles of 0.8 (6) and 12.1 (3)° with respect to the central pyridine ring. The mean planes of the corresponding methyl acetate groups form dihedral angles of 41.76 (13) and 86.48 (15)°, respectively with the mean plane of pyridine ring. A pair of weak intra-molecular N-H⋯N hydrogen bonds generate an S(5)S(5) ring motif in the mol-ecule. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds into [001] chains. The chains are cross-linked by C-H⋯O hydrogen bonds into layers lying parallel to bc plane. The crystal packing also features a C-H⋯π inter-action.

Related literature

For the synthesis and biological activity screening of some dipicolinic acid bis-l-amino acid hydrazide derivatives and their corresponding acids, see: Abou-Ghalia & Amr (2004 ▶); Al-Salahi et al. (2010 ▶); Al-Omar & Amr (2010 ▶); Attia et al. (2000 ▶). For the biological activity of 2,6-disubstituted pyridine derivatives, see: Amr (2005 ▶); Abou-Ghalia et al. (2003 ▶); Amr, Sayed & Abdulla (2005 ▶); Amr et al. (2006 ▶); Hammam et al. (2003 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H19N3O6

M = 337.33

Monoclinic,

a = 8.9735 (3) Å

b = 20.7073 (8) Å

c = 10.4048 (5) Å

β = 122.901 (3)°

V = 1623.29 (11) Å3

Z = 4

Cu Kα radiation

μ = 0.91 mm−1

T = 296 K

0.74 × 0.25 × 0.06 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.551, T max = 0.947

10358 measured reflections

2703 independent reflections

2058 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.192

S = 1.04

2703 reflections

229 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812022258/hb6780sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022258/hb6780Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812022258/hb6780Isup3.cml

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

C15H19N3O6	F(000) = 712
Mr = 337.33	Dx = 1.380 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 1828 reflections
a = 8.9735 (3) Å	θ = 5.5–70.4°
b = 20.7073 (8) Å	µ = 0.91 mm−1
c = 10.4048 (5) Å	T = 296 K
β = 122.901 (3)°	Plate, colourless
V = 1623.29 (11) Å3	0.74 × 0.25 × 0.06 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	2703 independent reflections
Radiation source: fine-focus sealed tube	2058 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
φ and ω scans	θmax = 65.0°, θmin = 5.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.551, Tmax = 0.947	k = −24→24
10358 measured reflections	l = −11→9

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.192	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.1344P)2] where P = (Fo2 + 2Fc2)/3
2703 reflections	(Δ/σ)max < 0.001
229 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.28 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
O1	−0.1466 (3)	0.53103 (10)	0.8205 (2)	0.0711 (6)
O2	0.4090 (3)	0.56823 (9)	0.89076 (19)	0.0641 (5)
O3	0.2864 (3)	0.49181 (10)	0.7100 (2)	0.0710 (6)
O4	0.2803 (2)	0.77285 (8)	1.37663 (16)	0.0578 (5)
O5	0.6292 (4)	0.83396 (18)	1.1329 (3)	0.1239 (11)
O6	0.3640 (4)	0.87058 (11)	1.0701 (2)	0.0823 (7)
N1	0.0899 (2)	0.66141 (9)	1.07033 (18)	0.0438 (5)
N2	0.0839 (3)	0.58945 (11)	0.8529 (2)	0.0602 (6)
N3	0.3295 (3)	0.75674 (9)	1.1876 (2)	0.0497 (5)
C1	0.0965 (3)	0.69752 (10)	1.1805 (2)	0.0449 (5)
C2	−0.0180 (4)	0.68863 (13)	1.2288 (3)	0.0584 (7)
H2A	−0.0101	0.7145	1.3054	0.070*
C3	−0.1448 (4)	0.64055 (14)	1.1610 (3)	0.0638 (7)
H3A	−0.2241	0.6337	1.1910	0.077*
C4	−0.1521 (4)	0.60292 (13)	1.0484 (3)	0.0572 (6)
H4A	−0.2358	0.5701	1.0016	0.069*
C5	−0.0334 (3)	0.61483 (11)	1.0065 (2)	0.0471 (5)
C6	−0.0374 (3)	0.57458 (12)	0.8840 (2)	0.0530 (6)
C7	0.0902 (4)	0.55753 (13)	0.7325 (3)	0.0607 (7)
H7A	0.0229	0.5172	0.7074	0.073*
C8	0.2796 (4)	0.54102 (12)	0.7893 (3)	0.0550 (6)
C9	0.4596 (4)	0.46969 (16)	0.7517 (3)	0.0766 (8)
H9A	0.4468	0.4353	0.6845	0.115*
H9B	0.5236	0.4543	0.8553	0.115*
H9C	0.5236	0.5047	0.7430	0.115*
C10	0.0058 (4)	0.59893 (17)	0.5880 (3)	0.0788 (9)
H10A	−0.1141	0.6092	0.5555	0.118*
H10B	0.0058	0.5755	0.5083	0.118*
H10C	0.0726	0.6381	0.6093	0.118*
C11	0.2444 (3)	0.74632 (10)	1.2579 (2)	0.0439 (5)
C12	0.4982 (3)	0.79021 (13)	1.2598 (3)	0.0566 (6)
H12A	0.5071	0.8179	1.3401	0.068*
C13	0.5066 (5)	0.83318 (16)	1.1474 (3)	0.0723 (9)
C14	0.3623 (7)	0.91492 (19)	0.9625 (4)	0.1168 (16)
H14A	0.2584	0.9416	0.9187	0.175*
H14B	0.3610	0.8911	0.8828	0.175*
H14C	0.4665	0.9416	1.0144	0.175*
C15	0.6504 (4)	0.74250 (17)	1.3363 (4)	0.0899 (10)
H15A	0.6515	0.7215	1.4191	0.135*
H15B	0.7605	0.7650	1.3753	0.135*
H15C	0.6356	0.7107	1.2630	0.135*
H1N3	0.289 (3)	0.7353 (11)	1.105 (3)	0.044 (6)*
H1N2	0.151 (4)	0.6210 (14)	0.896 (3)	0.063 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0754 (13)	0.0729 (12)	0.0837 (11)	−0.0269 (10)	0.0553 (11)	−0.0275 (9)
O2	0.0620 (12)	0.0660 (11)	0.0641 (9)	−0.0096 (9)	0.0342 (9)	−0.0117 (8)
O3	0.0754 (14)	0.0750 (12)	0.0845 (12)	−0.0149 (10)	0.0576 (11)	−0.0296 (9)
O4	0.0738 (12)	0.0660 (10)	0.0528 (8)	−0.0078 (9)	0.0469 (9)	−0.0110 (7)
O5	0.115 (2)	0.176 (3)	0.136 (2)	−0.051 (2)	0.1048 (19)	−0.031 (2)
O6	0.1178 (18)	0.0758 (13)	0.0865 (12)	−0.0121 (13)	0.0770 (13)	0.0060 (10)
N1	0.0479 (11)	0.0482 (10)	0.0445 (9)	0.0006 (8)	0.0310 (9)	0.0015 (7)
N2	0.0646 (14)	0.0696 (14)	0.0651 (11)	−0.0223 (12)	0.0473 (11)	−0.0253 (10)
N3	0.0573 (13)	0.0580 (11)	0.0470 (9)	−0.0132 (9)	0.0369 (10)	−0.0131 (8)
C1	0.0506 (13)	0.0491 (12)	0.0440 (9)	0.0040 (10)	0.0315 (10)	0.0047 (8)
C2	0.0720 (17)	0.0656 (15)	0.0631 (12)	−0.0023 (13)	0.0533 (13)	−0.0044 (10)
C3	0.0662 (16)	0.0735 (17)	0.0811 (15)	−0.0105 (14)	0.0591 (14)	−0.0040 (12)
C4	0.0602 (16)	0.0566 (14)	0.0705 (14)	−0.0088 (12)	0.0457 (13)	−0.0010 (10)
C5	0.0490 (13)	0.0486 (12)	0.0503 (10)	0.0000 (10)	0.0312 (11)	0.0019 (9)
C6	0.0542 (15)	0.0541 (13)	0.0569 (11)	−0.0060 (11)	0.0343 (12)	−0.0062 (10)
C7	0.0639 (16)	0.0681 (16)	0.0653 (13)	−0.0184 (13)	0.0450 (13)	−0.0261 (11)
C8	0.0679 (17)	0.0549 (13)	0.0589 (12)	−0.0104 (13)	0.0452 (13)	−0.0090 (10)
C9	0.085 (2)	0.083 (2)	0.0836 (17)	0.0065 (17)	0.0600 (17)	−0.0092 (14)
C10	0.072 (2)	0.105 (2)	0.0569 (13)	−0.0048 (18)	0.0335 (15)	−0.0183 (14)
C11	0.0519 (13)	0.0489 (12)	0.0430 (10)	0.0039 (10)	0.0337 (10)	0.0022 (8)
C12	0.0583 (15)	0.0647 (15)	0.0617 (12)	−0.0148 (12)	0.0422 (12)	−0.0206 (10)
C13	0.086 (2)	0.084 (2)	0.0764 (16)	−0.0386 (18)	0.0634 (17)	−0.0317 (15)
C14	0.197 (5)	0.094 (2)	0.095 (2)	−0.044 (3)	0.103 (3)	−0.0047 (18)
C15	0.0597 (19)	0.085 (2)	0.122 (2)	−0.0032 (16)	0.0471 (18)	−0.0272 (19)

O1—C6	1.227 (3)	C4—C5	1.375 (3)
O2—C8	1.204 (3)	C4—H4A	0.9300
O3—C8	1.334 (3)	C5—C6	1.507 (3)
O3—C9	1.442 (4)	C7—C8	1.504 (4)
O4—C11	1.225 (2)	C7—C10	1.527 (4)
O5—C13	1.189 (4)	C7—H7A	0.9800
O6—C13	1.329 (4)	C9—H9A	0.9600
O6—C14	1.441 (3)	C9—H9B	0.9600
N1—C5	1.340 (3)	C9—H9C	0.9600
N1—C1	1.343 (3)	C10—H10A	0.9600
N2—C6	1.329 (3)	C10—H10B	0.9600
N2—C7	1.445 (3)	C10—H10C	0.9600
N2—H1N2	0.83 (3)	C12—C13	1.504 (4)
N3—C11	1.331 (3)	C12—C15	1.514 (4)
N3—C12	1.449 (3)	C12—H12A	0.9800
N3—H1N3	0.85 (2)	C14—H14A	0.9600
C1—C2	1.379 (3)	C14—H14B	0.9600
C1—C11	1.507 (3)	C14—H14C	0.9600
C2—C3	1.383 (4)	C15—H15A	0.9600
C2—H2A	0.9300	C15—H15B	0.9600
C3—C4	1.378 (3)	C15—H15C	0.9600
C3—H3A	0.9300
C8—O3—C9	117.4 (2)	O3—C9—H9A	109.5
C13—O6—C14	116.2 (3)	O3—C9—H9B	109.5
C5—N1—C1	117.75 (19)	H9A—C9—H9B	109.5
C6—N2—C7	121.9 (2)	O3—C9—H9C	109.5
C6—N2—H1N2	119 (2)	H9A—C9—H9C	109.5
C7—N2—H1N2	118 (2)	H9B—C9—H9C	109.5
C11—N3—C12	122.81 (17)	C7—C10—H10A	109.5
C11—N3—H1N3	114.2 (17)	C7—C10—H10B	109.5
C12—N3—H1N3	121.7 (17)	H10A—C10—H10B	109.5
N1—C1—C2	122.7 (2)	C7—C10—H10C	109.5
N1—C1—C11	116.56 (19)	H10A—C10—H10C	109.5
C2—C1—C11	120.61 (19)	H10B—C10—H10C	109.5
C1—C2—C3	118.7 (2)	O4—C11—N3	124.5 (2)
C1—C2—H2A	120.7	O4—C11—C1	120.8 (2)
C3—C2—H2A	120.7	N3—C11—C1	114.65 (17)
C4—C3—C2	119.1 (2)	N3—C12—C13	111.0 (2)
C4—C3—H3A	120.4	N3—C12—C15	110.5 (2)
C2—C3—H3A	120.4	C13—C12—C15	112.5 (3)
C5—C4—C3	118.7 (2)	N3—C12—H12A	107.5
C5—C4—H4A	120.6	C13—C12—H12A	107.5
C3—C4—H4A	120.6	C15—C12—H12A	107.5
N1—C5—C4	123.0 (2)	O5—C13—O6	124.6 (3)
N1—C5—C6	116.8 (2)	O5—C13—C12	123.2 (4)
C4—C5—C6	120.1 (2)	O6—C13—C12	112.2 (2)
O1—C6—N2	124.0 (2)	O6—C14—H14A	109.5
O1—C6—C5	120.5 (2)	O6—C14—H14B	109.5
N2—C6—C5	115.5 (2)	H14A—C14—H14B	109.5
N2—C7—C8	109.3 (2)	O6—C14—H14C	109.5
N2—C7—C10	111.4 (2)	H14A—C14—H14C	109.5
C8—C7—C10	111.4 (2)	H14B—C14—H14C	109.5
N2—C7—H7A	108.2	C12—C15—H15A	109.5
C8—C7—H7A	108.2	C12—C15—H15B	109.5
C10—C7—H7A	108.2	H15A—C15—H15B	109.5
O2—C8—O3	123.6 (2)	C12—C15—H15C	109.5
O2—C8—C7	125.8 (2)	H15A—C15—H15C	109.5
O3—C8—C7	110.6 (2)	H15B—C15—H15C	109.5
C5—N1—C1—C2	−0.4 (3)	C9—O3—C8—C7	−179.5 (2)
C5—N1—C1—C11	175.80 (18)	N2—C7—C8—O2	−25.0 (4)
N1—C1—C2—C3	0.0 (4)	C10—C7—C8—O2	98.6 (3)
C11—C1—C2—C3	−176.0 (2)	N2—C7—C8—O3	156.0 (2)
C1—C2—C3—C4	0.4 (4)	C10—C7—C8—O3	−80.5 (3)
C2—C3—C4—C5	−0.4 (4)	C12—N3—C11—O4	13.6 (4)
C1—N1—C5—C4	0.3 (3)	C12—N3—C11—C1	−165.8 (2)
C1—N1—C5—C6	−179.55 (19)	N1—C1—C11—O4	−166.69 (19)
C3—C4—C5—N1	0.1 (4)	C2—C1—C11—O4	9.5 (3)
C3—C4—C5—C6	179.9 (2)	N1—C1—C11—N3	12.8 (3)
C7—N2—C6—O1	4.1 (4)	C2—C1—C11—N3	−171.0 (2)
C7—N2—C6—C5	−176.5 (2)	C11—N3—C12—C13	−141.6 (2)
N1—C5—C6—O1	180.0 (2)	C11—N3—C12—C15	92.8 (3)
C4—C5—C6—O1	0.1 (4)	C14—O6—C13—O5	−0.3 (4)
N1—C5—C6—N2	0.5 (3)	C14—O6—C13—C12	178.2 (2)
C4—C5—C6—N2	−179.3 (2)	N3—C12—C13—O5	−131.9 (3)
C6—N2—C7—C8	−136.0 (3)	C15—C12—C13—O5	−7.5 (4)
C6—N2—C7—C10	100.4 (3)	N3—C12—C13—O6	49.5 (3)
C9—O3—C8—O2	1.4 (4)	C15—C12—C13—O6	173.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···N1	0.85 (3)	2.23 (3)	2.676 (3)	113 (2)
N3—H1N3···O4i	0.85 (2)	2.35 (2)	3.080 (2)	145 (2)
N2—H1N2···N1	0.84 (3)	2.32 (3)	2.685 (3)	107 (3)
N2—H1N2···O4i	0.83 (3)	2.55 (3)	3.290 (3)	149 (2)
C9—H9B···O2ii	0.96	2.41	3.329 (3)	159
C15—H15B···Cg1iii	0.96	2.78	3.544 (4)	137

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C1–C5 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N3⋯N1	0.85 (3)	2.23 (3)	2.676 (3)	113 (2)
N3—H1N3⋯O4i	0.85 (2)	2.35 (2)	3.080 (2)	145 (2)
N2—H1N2⋯N1	0.84 (3)	2.32 (3)	2.685 (3)	107 (3)
N2—H1N2⋯O4i	0.83 (3)	2.55 (3)	3.290 (3)	149 (2)
C9—H9B⋯O2ii	0.96	2.41	3.329 (3)	159
C15—H15B⋯Cg1iii	0.96	2.78	3.544 (4)	137

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