Methyl 2-({6-[(1-meth-oxy-2-methyl-1-oxopropan-2-yl)carbamo-yl]pyridin-2-yl}formamido)-2-methyl-propano-ate.

In the title compound, C(17)H(23)N(3)O(6), the two meth-oxy-carbonyl C-O-C=O planes are inclined at dihedral angles of 5.3 (4) and 83.9 (4)° with respect to the central pyridine ring. An intra-molecular N-H⋯O hydrogen bond generates an S(5) ring motif. In the crystal, mol-ecules are linked into a chain along the c axis via C-H⋯O hydrogen bonds.

Related literature

For general background to and the pharmacological activity of the title compound, see: Abou-Ghalia & Amr (2004 ▶); Abou-Ghalia et al. (2003 ▶); Al-Omar & Amr (2010 ▶); Amr (2000 ▶); Attia et al. (1997 ▶, 2000 ▶); Amr et al. (2009 ▶); Fakhr et al. (2008 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H23N3O6

M = 365.38

Orthorhombic,

a = 10.2307 (10) Å

b = 9.3038 (11) Å

c = 20.652 (2) Å

V = 1965.8 (4) Å3

Z = 4

Cu Kα radiation

μ = 0.79 mm−1

T = 296 K

0.63 × 0.52 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.560, T max = 0.932

7477 measured reflections

1898 independent reflections

1249 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.133

S = 0.91

1898 reflections

250 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.17 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/S1600536812014651/is5109sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014651/is5109Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812014651/is5109Isup3.cml

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

C17H23N3O6	F(000) = 776
Mr = 365.38	Dx = 1.235 Mg m−3
Orthorhombic, Pca21	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2c -2ac	Cell parameters from 874 reflections
a = 10.2307 (10) Å	θ = 4.8–49.5°
b = 9.3038 (11) Å	µ = 0.79 mm−1
c = 20.652 (2) Å	T = 296 K
V = 1965.8 (4) Å3	Plate, colourless
Z = 4	0.63 × 0.52 × 0.09 mm

Bruker SMART APEXII CCD area-detector diffractometer	1898 independent reflections
Radiation source: fine-focus sealed tube	1249 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ and ω scans	θmax = 70.3°, θmin = 6.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→10
Tmin = 0.560, Tmax = 0.932	k = −10→11
7477 measured reflections	l = −24→13

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)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.133	w = 1/[σ2(Fo2) + (0.0914P)2] where P = (Fo2 + 2Fc2)/3
S = 0.91	(Δ/σ)max = 0.001
1898 reflections	Δρmax = 0.19 e Å−3
250 parameters	Δρmin = −0.17 e Å−3
1 restraint	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0102 (11)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.6692 (3)	0.7355 (4)	0.72873 (15)	0.1024 (10)
O2	0.8492 (3)	0.6849 (5)	0.51295 (18)	0.1213 (13)
O3	1.0304 (3)	0.5979 (4)	0.55776 (19)	0.1156 (12)
O4	0.2658 (2)	0.9156 (4)	0.46691 (14)	0.1017 (11)
O5	0.3806 (4)	0.6611 (7)	0.3829 (2)	0.1392 (17)
O6	0.3250 (4)	0.8241 (7)	0.3084 (2)	0.170 (2)
N1	0.5055 (3)	0.8326 (3)	0.58446 (14)	0.0676 (8)
N2	0.7327 (3)	0.7306 (4)	0.62369 (18)	0.0745 (8)
H1N2	0.715 (4)	0.744 (4)	0.584 (2)	0.068 (12)*
N3	0.4811 (3)	0.8725 (5)	0.45674 (16)	0.0830 (10)
H1N3	0.554 (5)	0.851 (5)	0.484 (3)	0.102 (14)*
C1	0.5188 (3)	0.8156 (4)	0.64814 (17)	0.0665 (9)
C2	0.4185 (4)	0.8403 (4)	0.69200 (19)	0.0740 (10)
H2A	0.4315	0.8263	0.7361	0.089*
C3	0.2992 (4)	0.8860 (5)	0.66876 (19)	0.0774 (10)
H3A	0.2308	0.9055	0.6971	0.093*
C4	0.2830 (3)	0.9021 (5)	0.60377 (18)	0.0737 (10)
H4A	0.2027	0.9306	0.5870	0.088*
C5	0.3875 (3)	0.8757 (4)	0.5630 (2)	0.0684 (9)
C6	0.6502 (3)	0.7562 (5)	0.67077 (17)	0.0720 (9)
C7	0.8613 (3)	0.6622 (4)	0.6287 (2)	0.0741 (9)
C8	0.9097 (4)	0.6522 (5)	0.5605 (2)	0.0862 (11)
C9	1.0870 (6)	0.5824 (10)	0.4936 (3)	0.147 (3)
H9A	1.1591	0.5165	0.4954	0.220*
H9B	1.1173	0.6742	0.4786	0.220*
H9C	1.0219	0.5462	0.4643	0.220*
C10	0.9549 (4)	0.7569 (6)	0.6675 (3)	0.1005 (15)
H10A	0.9658	0.8474	0.6458	0.151*
H10B	1.0381	0.7099	0.6712	0.151*
H10C	0.9196	0.7731	0.7100	0.151*
C11	0.8503 (6)	0.5137 (6)	0.6576 (3)	0.1151 (17)
H11A	0.7937	0.4559	0.6313	0.173*
H11B	0.8149	0.5205	0.7006	0.173*
H11C	0.9353	0.4703	0.6595	0.173*
C12	0.3733 (3)	0.8903 (5)	0.49148 (19)	0.0774 (11)
C13	0.4893 (4)	0.8851 (7)	0.3870 (2)	0.0988 (17)
C14	0.3863 (4)	0.7913 (10)	0.3552 (2)	0.121 (2)
C15	0.2980 (11)	0.5560 (12)	0.3517 (4)	0.212 (5)
H15A	0.3126	0.4633	0.3709	0.317*
H15B	0.3185	0.5520	0.3064	0.317*
H15C	0.2080	0.5827	0.3571	0.317*
C16	0.6234 (4)	0.8267 (9)	0.3661 (3)	0.135 (3)
H16A	0.6336	0.7301	0.3816	0.203*
H16B	0.6912	0.8862	0.3838	0.203*
H16C	0.6291	0.8273	0.3197	0.203*
C17	0.4747 (6)	1.0409 (9)	0.3669 (3)	0.143 (3)
H17A	0.4022	1.0830	0.3896	0.215*
H17B	0.4594	1.0461	0.3211	0.215*
H17C	0.5533	1.0924	0.3774	0.215*

	U11	U22	U33	U12	U13	U23
O1	0.101 (2)	0.140 (3)	0.0657 (19)	0.0175 (18)	−0.0122 (14)	0.0065 (18)
O2	0.096 (2)	0.188 (4)	0.080 (2)	0.027 (2)	0.0005 (17)	0.002 (2)
O3	0.0874 (19)	0.157 (3)	0.102 (3)	0.0322 (18)	0.0008 (16)	−0.005 (2)
O4	0.0631 (13)	0.167 (3)	0.0754 (17)	0.0001 (15)	−0.0090 (13)	0.0276 (19)
O5	0.133 (3)	0.200 (5)	0.085 (3)	−0.049 (3)	−0.009 (2)	−0.016 (3)
O6	0.114 (3)	0.318 (7)	0.078 (2)	−0.045 (4)	−0.038 (2)	0.024 (3)
N1	0.0623 (15)	0.085 (2)	0.0558 (18)	−0.0025 (14)	−0.0017 (11)	−0.0001 (14)
N2	0.0652 (15)	0.096 (2)	0.0620 (19)	0.0030 (14)	−0.0075 (14)	0.0038 (18)
N3	0.0638 (16)	0.130 (3)	0.0552 (18)	0.0040 (16)	−0.0019 (13)	0.0054 (17)
C1	0.0708 (19)	0.074 (2)	0.054 (2)	−0.0044 (15)	−0.0051 (14)	0.0036 (17)
C2	0.085 (2)	0.080 (2)	0.057 (2)	−0.0078 (18)	0.0009 (17)	−0.005 (2)
C3	0.071 (2)	0.090 (3)	0.071 (3)	−0.0034 (19)	0.0125 (17)	−0.008 (2)
C4	0.0646 (19)	0.088 (3)	0.068 (2)	−0.0023 (17)	0.0045 (15)	−0.0001 (19)
C5	0.0603 (17)	0.081 (2)	0.064 (2)	−0.0025 (15)	−0.0025 (15)	−0.0004 (18)
C6	0.075 (2)	0.087 (3)	0.054 (2)	−0.0019 (18)	−0.0104 (16)	0.0023 (18)
C7	0.0707 (19)	0.079 (2)	0.072 (2)	0.0061 (17)	−0.0080 (17)	0.001 (2)
C8	0.072 (2)	0.101 (3)	0.086 (3)	0.0066 (19)	−0.005 (2)	−0.004 (3)
C9	0.104 (4)	0.217 (8)	0.118 (4)	0.037 (4)	0.019 (3)	−0.021 (5)
C10	0.078 (2)	0.123 (4)	0.100 (3)	0.012 (2)	−0.020 (2)	−0.019 (3)
C11	0.125 (4)	0.100 (4)	0.121 (4)	0.025 (3)	0.010 (3)	0.021 (3)
C12	0.0661 (19)	0.105 (3)	0.061 (2)	−0.0039 (18)	−0.0013 (16)	0.008 (2)
C13	0.066 (2)	0.174 (5)	0.056 (2)	−0.004 (2)	−0.0016 (15)	0.014 (3)
C14	0.086 (3)	0.222 (7)	0.056 (3)	−0.027 (3)	−0.004 (2)	0.012 (4)
C15	0.227 (10)	0.274 (12)	0.134 (6)	−0.117 (9)	−0.011 (6)	−0.065 (7)
C16	0.076 (3)	0.249 (8)	0.081 (3)	−0.005 (3)	0.010 (2)	−0.032 (4)
C17	0.111 (4)	0.213 (8)	0.106 (4)	−0.015 (4)	0.003 (3)	0.066 (5)

O1—C6	1.228 (5)	C7—C8	1.497 (6)
O2—C8	1.200 (6)	C7—C11	1.509 (7)
O3—C8	1.335 (5)	C7—C10	1.528 (6)
O3—C9	1.454 (7)	C9—H9A	0.9600
O4—C12	1.234 (4)	C9—H9B	0.9600
O5—C14	1.341 (9)	C9—H9C	0.9600
O5—C15	1.444 (8)	C10—H10A	0.9600
O6—C14	1.191 (6)	C10—H10B	0.9600
N1—C1	1.332 (5)	C10—H10C	0.9600
N1—C5	1.347 (4)	C11—H11A	0.9600
N2—C6	1.309 (5)	C11—H11B	0.9600
N2—C7	1.466 (5)	C11—H11C	0.9600
N2—H1N2	0.84 (4)	C13—C17	1.516 (9)
N3—C12	1.326 (5)	C13—C14	1.518 (8)
N3—C13	1.447 (6)	C13—C16	1.538 (7)
N3—H1N3	0.95 (5)	C15—H15A	0.9600
C1—C2	1.387 (5)	C15—H15B	0.9600
C1—C6	1.527 (5)	C15—H15C	0.9600
C2—C3	1.379 (6)	C16—H16A	0.9600
C2—H2A	0.9300	C16—H16B	0.9600
C3—C4	1.361 (6)	C16—H16C	0.9600
C3—H3A	0.9300	C17—H17A	0.9600
C4—C5	1.382 (5)	C17—H17B	0.9600
C4—H4A	0.9300	C17—H17C	0.9600
C5—C12	1.491 (6)
C8—O3—C9	116.4 (4)	C7—C10—H10A	109.5
C14—O5—C15	116.6 (7)	C7—C10—H10B	109.5
C1—N1—C5	116.8 (3)	H10A—C10—H10B	109.5
C6—N2—C7	127.2 (4)	C7—C10—H10C	109.5
C6—N2—H1N2	123 (3)	H10A—C10—H10C	109.5
C7—N2—H1N2	109 (3)	H10B—C10—H10C	109.5
C12—N3—C13	125.2 (3)	C7—C11—H11A	109.5
C12—N3—H1N3	111 (3)	C7—C11—H11B	109.5
C13—N3—H1N3	123 (3)	H11A—C11—H11B	109.5
N1—C1—C2	123.4 (3)	C7—C11—H11C	109.5
N1—C1—C6	115.8 (3)	H11A—C11—H11C	109.5
C2—C1—C6	120.7 (3)	H11B—C11—H11C	109.5
C3—C2—C1	118.6 (4)	O4—C12—N3	122.9 (4)
C3—C2—H2A	120.7	O4—C12—C5	120.8 (3)
C1—C2—H2A	120.7	N3—C12—C5	116.3 (3)
C4—C3—C2	119.0 (4)	N3—C13—C17	110.1 (5)
C4—C3—H3A	120.5	N3—C13—C14	110.1 (4)
C2—C3—H3A	120.5	C17—C13—C14	111.3 (5)
C3—C4—C5	119.1 (4)	N3—C13—C16	107.6 (4)
C3—C4—H4A	120.4	C17—C13—C16	110.4 (5)
C5—C4—H4A	120.4	C14—C13—C16	107.2 (5)
N1—C5—C4	123.1 (4)	O6—C14—O5	123.7 (7)
N1—C5—C12	116.1 (3)	O6—C14—C13	124.6 (8)
C4—C5—C12	120.8 (3)	O5—C14—C13	111.4 (4)
O1—C6—N2	126.4 (4)	O5—C15—H15A	109.5
O1—C6—C1	119.7 (4)	O5—C15—H15B	109.5
N2—C6—C1	114.0 (3)	H15A—C15—H15B	109.5
N2—C7—C8	104.9 (3)	O5—C15—H15C	109.5
N2—C7—C11	111.0 (4)	H15A—C15—H15C	109.5
C8—C7—C11	109.9 (4)	H15B—C15—H15C	109.5
N2—C7—C10	110.5 (3)	C13—C16—H16A	109.5
C8—C7—C10	108.8 (4)	C13—C16—H16B	109.5
C11—C7—C10	111.6 (4)	H16A—C16—H16B	109.5
O2—C8—O3	122.6 (4)	C13—C16—H16C	109.5
O2—C8—C7	125.8 (4)	H16A—C16—H16C	109.5
O3—C8—C7	111.7 (4)	H16B—C16—H16C	109.5
O3—C9—H9A	109.5	C13—C17—H17A	109.5
O3—C9—H9B	109.5	C13—C17—H17B	109.5
H9A—C9—H9B	109.5	H17A—C17—H17B	109.5
O3—C9—H9C	109.5	C13—C17—H17C	109.5
H9A—C9—H9C	109.5	H17A—C17—H17C	109.5
H9B—C9—H9C	109.5	H17B—C17—H17C	109.5
C5—N1—C1—C2	−0.2 (5)	C11—C7—C8—O2	114.7 (6)
C5—N1—C1—C6	175.6 (4)	C10—C7—C8—O2	−122.9 (5)
N1—C1—C2—C3	−0.6 (6)	N2—C7—C8—O3	176.8 (4)
C6—C1—C2—C3	−176.2 (4)	C11—C7—C8—O3	−63.8 (5)
C1—C2—C3—C4	1.5 (6)	C10—C7—C8—O3	58.6 (5)
C2—C3—C4—C5	−1.6 (7)	C13—N3—C12—O4	2.3 (8)
C1—N1—C5—C4	0.1 (6)	C13—N3—C12—C5	−178.6 (4)
C1—N1—C5—C12	−178.4 (4)	N1—C5—C12—O4	173.0 (4)
C3—C4—C5—N1	0.8 (7)	C4—C5—C12—O4	−5.5 (7)
C3—C4—C5—C12	179.2 (4)	N1—C5—C12—N3	−6.1 (6)
C7—N2—C6—O1	4.9 (7)	C4—C5—C12—N3	175.4 (4)
C7—N2—C6—C1	−174.3 (3)	C12—N3—C13—C17	70.9 (6)
N1—C1—C6—O1	−178.9 (4)	C12—N3—C13—C14	−52.2 (7)
C2—C1—C6—O1	−3.0 (6)	C12—N3—C13—C16	−168.7 (5)
N1—C1—C6—N2	0.3 (5)	C15—O5—C14—O6	2.2 (10)
C2—C1—C6—N2	176.3 (4)	C15—O5—C14—C13	−172.4 (6)
C6—N2—C7—C8	176.8 (4)	N3—C13—C14—O6	141.2 (6)
C6—N2—C7—C11	58.1 (6)	C17—C13—C14—O6	18.8 (8)
C6—N2—C7—C10	−66.1 (5)	C16—C13—C14—O6	−102.1 (8)
C9—O3—C8—O2	1.1 (8)	N3—C13—C14—O5	−44.3 (6)
C9—O3—C8—C7	179.6 (5)	C17—C13—C14—O5	−166.7 (5)
N2—C7—C8—O2	−4.7 (6)	C16—C13—C14—O5	72.4 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2	0.85 (4)	2.08 (4)	2.614 (5)	120 (3)
C3—H3A···O6i	0.93	2.49	3.204 (6)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O2	0.85 (4)	2.08 (4)	2.614 (5)	120 (3)
C3—H3A⋯O6i	0.93	2.49	3.204 (6)	134

Symmetry code: (i) .