Methyl 2-({6-[(1-meth­oxy-2-methyl-1-oxopropan-2-yl)carbamo­yl]pyridin-2-yl}formamido)-2-methyl­propano­ate

Al-Omar, M.A.; Amr, A.-G.E.; Ghabbour, H.A.; Quah, C.K.; Fun, H.-K.

doi:10.1107/S1600536812014651

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1377-o1378

doi:10.1107/S1600536812014651

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Methyl 2-({6-[(1-methoxy-2-methyl-1-oxopropan-2-yl)carbamoyl]pyridin-2-yl}formamido)-2-methylpropanoate

Mohamed A. Al-Omar,^a,^b Abdel-Galil E. Amr,^b,^c Hazem A. Ghabbour,^a Ching Kheng Quah ^d ‡ and Hoong-Kun Fun ^d ^*§

^aPharmaceutical Chemistry Department, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^bDrug Exploration & Development Chair (DEDC), College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^cApplied Organic Chemistry Department, National Research Center, Dokki 12622, Cairo, Egypt, and ^dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 28 March 2012; accepted 4 April 2012; online 13 April 2012)

In the title compound, C₁₇H₂₃N₃O₆, the two methoxycarbonyl 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 intramolecular N—H⋯O hydrogen bond generates an S(5) ring motif. In the crystal, molecules 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_r = 365.38
Orthorhombic, P c a 2₁
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[F² > 2σ(F²)] = 0.050
wR(F²) = 0.133
S = 0.91
1898 reflections
250 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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) $[-x+{\script{1\over 2}}, y, z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812014651/is5109sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812014651/is5109Isup3.cml

checkCIF report

Comment top

In our previous work, we have reported that certain substituted pyridines and Schiff base derivatives are antimicrobial, anti-inflammatory and anticancer agents (Abou-Ghalia & Amr, 2004; Abou-Ghalia et al., 2003; Al-Omar & Amr, 2010; Amr, 2000; Attia et al., 1997, 2000). In continuation of our interests in the chemical and pharmacological properties of disubstituted pyridine derivatives (Amr et al., 2009; Fakhr et al., 2008), we report herein the synthesis and antimicrobial activities of the title compound.

In the title molecule (Fig. 1), the two methoxycarbonyl moieties (O2/O3/C8/C9 and O5/O6/C14/C15) are nearly planar [maximum deviations of 0.005 (5) and 0.009 (5) Å at atoms C8 and C14, respectively] and are inclined at angles of 5.3 (4) and 83.9 (4)° with the pyridine ring (N1/C1–C5). Bond lengths (Allen et al., 1987) and angles are within normal ranges. The molecular structure is stabilized by an intramolecular N2—H1N2···O2 hydrogen bond (Table 1), which generates an S(5) ring motif (Bernstein et al., 1995).

In the crystal (Fig. 2), molecules are linked into one-dimensional chains propagating along the [001] direction via intermolecular C3—H3A···O6 hydrogen bonds (Table 1).

Related literature top

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 top

To a solution of 2-methylalanine methyl esters (2 mmol), 2,6-pyridinedicarboyl dichloride (1 mmol) in dichloromethane (15 mL) was added at -10 °C with stirring. Triethylamine was added drop wise to the reaction mixture in order to keep the reaction mixture slightly basic (pH ~ 8). Stirring was continued for 3 h more at -15 °C and then 12 h at r.t. The reaction mixture was then washed with water, 1N hydrochloric acid, 1N sodium bicarbonate and finally with water and dried over anhydrous calcium chloride. The solvent was evaporated under reduced pressure to dryness and the obtained solid was crystallized from chloroform to give the titled bis-ester.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids for non-H atoms. The intramolecular hydrogen bond is shown as a dashed line.
	Fig. 2. A crystal packing diagram of the title compound, viewed along the b axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

Methyl 2-({6-[(1-methoxy-2-methyl-1-oxopropan-2- yl)carbamoyl]pyridin-2-yl}formamido)-2-methylpropanoate top

Crystal data top

C₁₇H₂₃N₃O₆	F(000) = 776
M_r = 365.38	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0914P)²] where P = (F_o² + 2F_c²)/3
S = 0.91	(Δ/σ)_max = 0.001
1898 reflections	Δρ_max = 0.19 e Å⁻³
250 parameters	Δρ_min = −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)

Crystal data top

C₁₇H₂₃N₃O₆	V = 1965.8 (4) Å³
M_r = 365.38	Z = 4
Orthorhombic, Pca2₁	Cu Kα radiation
a = 10.2307 (10) Å	µ = 0.79 mm⁻¹
b = 9.3038 (11) Å	T = 296 K
c = 20.652 (2) Å	0.63 × 0.52 × 0.09 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	1898 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1249 reflections with I > 2σ(I)
T_min = 0.560, T_max = 0.932	R_int = 0.043
7477 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	1 restraint
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	Δρ_max = 0.19 e Å⁻³
1898 reflections	Δρ_min = −0.17 e Å⁻³
250 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₃N₃O₆
M_r	365.38
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	296
a, b, c (Å)	10.2307 (10), 9.3038 (11), 20.652 (2)
V (Å³)	1965.8 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.79
Crystal size (mm)	0.63 × 0.52 × 0.09

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.560, 0.932
No. of measured, independent and observed [I > 2σ(I)] reflections	7477, 1898, 1249
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.133, 0.91
No. of reflections	1898
No. of parameters	250
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.17

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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	0.9300	2.4900	3.204 (6)	134.00

Symmetry code: (i) −x+1/2, y, z+1/2.

Footnotes

‡Thomson Reuters ResearcherID: A-5525-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors extend their appreciation to the Deanship of Scientific Research at King Saud University for funding this work through the research group project No. RGP-VPP-099.

References

Abou-Ghalia, M. H. & Amr, A. E. (2004). Amino Acids, 26, 283–289. Web of Science PubMed Google Scholar
Abou-Ghalia, M. H., Amr, A. E. & Abdulla, M. M. (2003). Z. Naturforsch. Teil B, 58, 903–910. Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Al-Omar, M. A. & Amr, A. E. (2010). Molecules, 15, 4711–4721. Web of Science CAS PubMed Google Scholar
Amr, A. E. (2000). Indian J. Heterocycl. Chem. 10, 49–58. Google Scholar
Amr, A. E., Sabrry, N. M., Abdalla, M. M. & Abdel-Wahab, B. F. (2009). Eur. J. Med. Chem. 44, 725–735. Web of Science CrossRef PubMed CAS Google Scholar
Attia, A., Abdel-Salam, O. I. & Amr, A. E. (1997). Egypt. J. Chem. 40, 317–325. CAS Google Scholar
Attia, A., Abdel-Salam, O. I. & Amr, A. E. (2000). Egypt. J. Chem. 43, 297–307. CAS Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fakhr, I. M., Amr, A. E., Sabry, N. M. & Abdalah, M. M. (2008). Arch. Pharm. Chem. Life Sci. 341, 174–180. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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