Ethyl 7-pivaloyl­amino-1,8-naphthyridine-2-carboxyl­ate sesquihydrate

Fun, H.-K.; Hemamalini, M.; Hazra, A.; Goswami, S.

doi:10.1107/S160053681104921X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3415

https://doi.org/10.1107/S160053681104921X

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Ethyl 7-pivaloylamino-1,8-naphthyridine-2-carboxylate sesquihydrate

Hoong-Kun Fun,^a ^*‡ Madhukar Hemamalini,^a Anita Hazra ^b and Shyamaprosad Goswami ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Bengal Engineering and Science University, Shibpur, Howrah 711 103, India
^*Correspondence e-mail: hkfun@usm.my

(Received 11 November 2011; accepted 18 November 2011; online 25 November 2011)

In the title hydrate, C₁₆H₁₉N₃O₃·1.5H₂O, both water molecules are disordered: one over two adjacent sites in a 0.498 (5):0.502 (5) ratio and one lying near a crystallographic twofold axis. The dihedral angle between the pyridine rings of the organic moleucle is 1.47 (6)°. In the crystal, the components are linked by N—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds, forming sheets lying parallel to the ac plane.

Related literature

For further details of heterocyclic esters, see: Listvan et al. (2002 ); Li et al. (2007 ); Goswami & Hazra (2009 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₆H₁₉N₃O₃·1.5H₂O
M_r = 656.73
Monoclinic, C 2/c
a = 30.7759 (7) Å
b = 7.2406 (2) Å
c = 16.9271 (4) Å
β = 120.009 (1)°
V = 3266.32 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.41 × 0.31 × 0.24 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.960, T_max = 0.977
16624 measured reflections
3753 independent reflections
3156 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.108
S = 1.04
3753 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N3⋯O2W	0.85	2.39	3.051 (2)	135
N3—H1N3⋯O1WBⁱ	0.85	2.40	3.095 (3)	140
O1WB—H2WB⋯N2	0.86	2.26	3.077 (3)	160
O2W—H1W2⋯N1ⁱ	0.83	2.13	2.948 (2)	167
C3—H3A⋯O3	0.93	2.23	2.8230 (17)	121
Symmetry code: (i) $[-x, y, -z+{\script{1\over 2}}]$ .

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: https://doi.org/10.1107/S160053681104921X/hb6505sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681104921X/hb6505Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681104921X/hb6505Isup3.cml

checkCIF report

Comment top

Heterocyclic esters are important synthons for the synthesis of different natural products, antimicrobial agents and pharmaceutical compositions (Listvan et al., 2002; Li et al., 2007). The heterocyclic esters are easily synthesized from their corresponding aldehydes by using thiamine hydrochloride as a catalyst in the presence of triethyl amine and alcohol (Goswami & Hazra, 2009). Herein we report the crystal structure of ethyl-7-pivaloylamino-[1,8]naphthyridine-2-carboxylate.

The asymmetric unit of the title compound, Fig. 1, consists of one ethyl-7-pivaloylamino-[1,8]naphthyridine-2-carboxylate molecule, one disordered water molecule over two orientations with a refined occupany ratio of 0.498 (5) : 0.502 (5) and a half-molecule of water (the O2W atom of the water molecule lies near a twofold axis (symmetry code: -x, y, -z+1/2). The dihedral angle between the two pyridine (N1/C1–C5 : N2/C1,C5–C8) rings is 1.47 (6)°.

In the crystal structure, (Fig. 2), the components are connected via intermolecular N—H···O, O—H···N and C—H···O hydrogen bonds (Table 1) to form two-dimensional networks parallel to the ac-plane.

Related literature top

For further details of heterocyclic esters, see: Listvan et al. (2002); Li et al. (2007); Goswami & Hazra (2009). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

Distilled triethylamine (0.6 ml) was added dropwise to a solution of 7-pivaloylamino-[1,8]naphthyridine-2-carbaldehyde (514 mg, 2 mmol) in dry ethanol. Then thiamine hydrochloride (30 mg, 15 mol) was added and the reaction mixture was refluxed for 2.5 h. Excess ethanol was distilled from the reaction mixture after completion of the reaction. Water was added to the reaction mixture and then extracted with chloroform and the organic layer was dried. The crude product was purified through column chromatography (silica gel, 100–200 mesh) eluting with ethyl acetate in petroleum ether (30%) to afford a colorless solid. Yield: 82%. Mp 168–170°C.

Structure description top

For further details of heterocyclic esters, see: Listvan et al. (2002); Li et al. (2007); Goswami & Hazra (2009). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

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 asymmetric unit of the title compound, showing 30% probability displacement ellipsoids. Open bonds reprents disorder components.
	Fig. 2. The crystal packing of the title compound (I). H atoms are not involing the hydrogen bond interactions are omitted for clarity.

Ethyl 7-pivaloylamino-1,8-naphthyridine-2-carboxylate sesquihydrate top

Crystal data top

C₁₆H₁₉N₃O₃·1.5H₂O	F(000) = 1400
M_r = 656.73	D_x = 1.335 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6305 reflections
a = 30.7759 (7) Å	θ = 2.9–33.5°
b = 7.2406 (2) Å	µ = 0.10 mm⁻¹
c = 16.9271 (4) Å	T = 100 K
β = 120.009 (1)°	Block, colourless
V = 3266.32 (14) Å³	0.41 × 0.31 × 0.24 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	3753 independent reflections
Radiation source: fine-focus sealed tube	3156 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
φ and ω scans	θ_max = 27.5°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −39→39
T_min = 0.960, T_max = 0.977	k = −9→9
16624 measured reflections	l = −21→21

Refinement top

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0531P)² + 2.3589P] where P = (F_o² + 2F_c²)/3
3753 reflections	(Δ/σ)_max < 0.001
228 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₆H₁₉N₃O₃·1.5H₂O	V = 3266.32 (14) Å³
M_r = 656.73	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 30.7759 (7) Å	µ = 0.10 mm⁻¹
b = 7.2406 (2) Å	T = 100 K
c = 16.9271 (4) Å	0.41 × 0.31 × 0.24 mm
β = 120.009 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3753 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3156 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.977	R_int = 0.030
16624 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.04	Δρ_max = 0.34 e Å⁻³
3753 reflections	Δρ_min = −0.23 e Å⁻³
228 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
O1	0.16006 (3)	0.48093 (13)	0.67950 (6)	0.0212 (2)
O2	0.14079 (3)	0.47791 (13)	0.53237 (6)	0.0232 (2)
O3	−0.17328 (4)	−0.00262 (19)	0.24944 (7)	0.0422 (3)
N1	−0.02737 (4)	0.20833 (14)	0.37662 (7)	0.0172 (2)
N2	0.04907 (4)	0.32379 (14)	0.48603 (7)	0.0166 (2)
N3	−0.10204 (4)	0.10828 (17)	0.25947 (7)	0.0245 (3)
H1N3	−0.0879	0.1349	0.2290	0.029*
C1	0.00362 (4)	0.25427 (15)	0.46599 (8)	0.0154 (2)
C2	−0.07277 (4)	0.14680 (16)	0.35245 (8)	0.0173 (2)
C3	−0.09081 (4)	0.12125 (17)	0.41469 (8)	0.0186 (2)
H3A	−0.1231	0.0774	0.3947	0.022*
C4	−0.05950 (4)	0.16280 (17)	0.50400 (8)	0.0186 (2)
H4A	−0.0701	0.1455	0.5462	0.022*
C5	−0.01072 (4)	0.23240 (16)	0.53302 (8)	0.0161 (2)
C6	0.02364 (4)	0.28315 (17)	0.62367 (8)	0.0187 (2)
H6A	0.0154	0.2698	0.6693	0.022*
C7	0.06941 (4)	0.35249 (16)	0.64349 (8)	0.0182 (2)
H7A	0.0928	0.3873	0.7027	0.022*
C8	0.08024 (4)	0.36993 (15)	0.57230 (8)	0.0160 (2)
C9	0.12989 (4)	0.44831 (16)	0.59031 (8)	0.0171 (2)
C10	0.20924 (4)	0.55545 (19)	0.70542 (9)	0.0232 (3)
H10A	0.2061	0.6797	0.6817	0.028*
H10B	0.2258	0.4789	0.6813	0.028*
C11	0.23881 (5)	0.5572 (2)	0.80776 (9)	0.0268 (3)
H11A	0.2718	0.6046	0.8277	0.040*
H11B	0.2413	0.4337	0.8303	0.040*
H11C	0.2222	0.6343	0.8307	0.040*
C12	−0.14904 (4)	0.03205 (16)	0.21292 (8)	0.0180 (2)
C13	−0.16825 (4)	−0.01579 (17)	0.11242 (8)	0.0194 (3)
C14	−0.14824 (5)	−0.20988 (19)	0.11108 (9)	0.0266 (3)
H14A	−0.1603	−0.2964	0.1386	0.040*
H14B	−0.1122	−0.2084	0.1447	0.040*
H14C	−0.1597	−0.2459	0.0492	0.040*
C15	−0.15098 (5)	0.1224 (2)	0.06522 (9)	0.0285 (3)
H15A	−0.1599	0.2452	0.0732	0.043*
H15B	−0.1669	0.0943	0.0013	0.043*
H15C	−0.1152	0.1144	0.0916	0.043*
C16	−0.22570 (5)	−0.02054 (19)	0.06234 (9)	0.0243 (3)
H16A	−0.2382	0.0996	0.0645	0.037*
H16B	−0.2366	−0.1086	0.0912	0.037*
H16C	−0.2383	−0.0557	−0.0001	0.037*
O1WB	0.05785 (9)	0.3977 (4)	0.31552 (15)	0.0289 (7)	0.502 (5)
H1WB	0.0755	0.4935	0.3217	0.035*	0.502 (5)
H2WB	0.0480	0.3869	0.3546	0.035*	0.502 (5)
O1WA	0.04715 (6)	0.4721 (2)	0.32308 (11)	0.0310 (7)	0.498 (5)
H1WA	0.0227	0.4263	0.2743	0.037*	0.498 (5)
H2WA	0.0604	0.4032	0.3761	0.037*	0.498 (5)
O2W	−0.01311 (6)	0.0366 (2)	0.23101 (11)	0.0245 (5)	0.50
H1W2	−0.0004	0.0990	0.2065	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0167 (4)	0.0275 (5)	0.0172 (4)	−0.0053 (3)	0.0067 (4)	−0.0017 (4)
O2	0.0228 (4)	0.0271 (5)	0.0213 (5)	−0.0056 (4)	0.0122 (4)	−0.0029 (4)
O3	0.0269 (5)	0.0798 (9)	0.0222 (5)	−0.0244 (5)	0.0140 (4)	−0.0140 (5)
N1	0.0174 (5)	0.0176 (5)	0.0162 (5)	−0.0011 (4)	0.0081 (4)	−0.0005 (4)
N2	0.0170 (5)	0.0149 (5)	0.0173 (5)	−0.0006 (4)	0.0081 (4)	−0.0004 (4)
N3	0.0195 (5)	0.0393 (7)	0.0165 (5)	−0.0083 (5)	0.0104 (4)	−0.0046 (5)
C1	0.0174 (5)	0.0120 (5)	0.0167 (6)	0.0013 (4)	0.0084 (5)	0.0010 (4)
C2	0.0178 (5)	0.0163 (5)	0.0172 (6)	0.0003 (4)	0.0082 (5)	−0.0010 (5)
C3	0.0164 (5)	0.0189 (6)	0.0218 (6)	−0.0005 (4)	0.0104 (5)	−0.0006 (5)
C4	0.0202 (6)	0.0192 (6)	0.0199 (6)	−0.0002 (5)	0.0126 (5)	0.0005 (5)
C5	0.0174 (5)	0.0143 (5)	0.0171 (6)	0.0013 (4)	0.0089 (5)	0.0004 (4)
C6	0.0220 (6)	0.0196 (6)	0.0160 (6)	0.0004 (5)	0.0107 (5)	0.0005 (5)
C7	0.0189 (5)	0.0176 (6)	0.0153 (6)	0.0000 (4)	0.0065 (5)	−0.0006 (5)
C8	0.0172 (5)	0.0119 (5)	0.0176 (6)	0.0013 (4)	0.0077 (5)	0.0004 (4)
C9	0.0188 (5)	0.0134 (5)	0.0181 (6)	0.0006 (4)	0.0084 (5)	−0.0004 (4)
C10	0.0164 (6)	0.0280 (7)	0.0234 (7)	−0.0057 (5)	0.0085 (5)	−0.0015 (5)
C11	0.0202 (6)	0.0318 (7)	0.0237 (7)	−0.0012 (5)	0.0074 (5)	−0.0044 (6)
C12	0.0157 (5)	0.0180 (6)	0.0180 (6)	0.0006 (4)	0.0066 (5)	−0.0008 (5)
C13	0.0180 (6)	0.0212 (6)	0.0177 (6)	−0.0023 (5)	0.0080 (5)	−0.0019 (5)
C14	0.0286 (7)	0.0278 (7)	0.0238 (7)	0.0021 (5)	0.0134 (6)	−0.0053 (5)
C15	0.0275 (7)	0.0350 (8)	0.0178 (6)	−0.0094 (6)	0.0075 (5)	0.0013 (5)
C16	0.0180 (6)	0.0298 (7)	0.0205 (6)	−0.0023 (5)	0.0061 (5)	−0.0036 (5)
O1WB	0.0291 (12)	0.0366 (15)	0.0210 (11)	0.0019 (10)	0.0126 (9)	0.0000 (10)
O1WA	0.0325 (13)	0.0350 (16)	0.0315 (12)	−0.0090 (11)	0.0204 (10)	−0.0005 (11)
O2W	0.0314 (13)	0.0251 (8)	0.0243 (14)	−0.0066 (7)	0.0193 (11)	−0.0056 (7)

Geometric parameters (Å, º) top

O1—C9	1.3397 (15)	C11—H11A	0.9600
O1—C10	1.4527 (14)	C11—H11B	0.9600
O2—C9	1.2038 (15)	C11—H11C	0.9600
O3—C12	1.2097 (15)	C12—C13	1.5353 (17)
N1—C2	1.3213 (15)	C13—C16	1.5319 (17)
N1—C1	1.3659 (15)	C13—C15	1.5321 (17)
N2—C8	1.3278 (15)	C13—C14	1.5392 (18)
N2—C1	1.3604 (15)	C14—H14A	0.9600
N3—C12	1.3703 (15)	C14—H14B	0.9600
N3—C2	1.3958 (15)	C14—H14C	0.9600
N3—H1N3	0.8462	C15—H15A	0.9600
C1—C5	1.4170 (16)	C15—H15B	0.9600
C2—C3	1.4275 (16)	C15—H15C	0.9600
C3—C4	1.3592 (17)	C16—H16A	0.9600
C3—H3A	0.9300	C16—H16B	0.9600
C4—C5	1.4182 (16)	C16—H16C	0.9600
C4—H4A	0.9300	O1WB—H1WB	0.8550
C5—C6	1.4089 (17)	O1WB—H2WB	0.8586
C6—C7	1.3698 (16)	O1WB—H1WA	0.9712
C6—H6A	0.9300	O1WB—H2WA	0.9888
C7—C8	1.4073 (16)	O1WA—H1WB	0.8984
C7—H7A	0.9300	O1WA—H2WB	0.8078
C8—C9	1.5114 (16)	O1WA—H1WA	0.8576
C10—C11	1.5008 (18)	O1WA—H2WA	0.9243
C10—H10A	0.9700	O2W—O2Wⁱ	0.739 (3)
C10—H10B	0.9700	O2W—H1W2	0.8319

C9—O1—C10	115.85 (9)	C10—C11—H11C	109.5
C2—N1—C1	118.01 (10)	H11A—C11—H11C	109.5
C8—N2—C1	117.02 (10)	H11B—C11—H11C	109.5
C12—N3—C2	129.00 (10)	O3—C12—N3	122.22 (12)
C12—N3—H1N3	117.2	O3—C12—C13	121.68 (11)
C2—N3—H1N3	113.8	N3—C12—C13	116.03 (10)
N2—C1—N1	115.32 (10)	C16—C13—C15	109.37 (11)
N2—C1—C5	122.34 (11)	C16—C13—C12	108.45 (10)
N1—C1—C5	122.34 (10)	C15—C13—C12	112.87 (10)
N1—C2—N3	113.75 (10)	C16—C13—C14	109.33 (10)
N1—C2—C3	123.82 (11)	C15—C13—C14	110.05 (11)
N3—C2—C3	122.44 (10)	C12—C13—C14	106.69 (10)
C4—C3—C2	118.10 (10)	C13—C14—H14A	109.5
C4—C3—H3A	121.0	C13—C14—H14B	109.5
C2—C3—H3A	121.0	H14A—C14—H14B	109.5
C3—C4—C5	120.18 (11)	C13—C14—H14C	109.5
C3—C4—H4A	119.9	H14A—C14—H14C	109.5
C5—C4—H4A	119.9	H14B—C14—H14C	109.5
C6—C5—C1	118.57 (10)	C13—C15—H15A	109.5
C6—C5—C4	123.90 (11)	C13—C15—H15B	109.5
C1—C5—C4	117.52 (11)	H15A—C15—H15B	109.5
C7—C6—C5	118.82 (11)	C13—C15—H15C	109.5
C7—C6—H6A	120.6	H15A—C15—H15C	109.5
C5—C6—H6A	120.6	H15B—C15—H15C	109.5
C6—C7—C8	118.56 (11)	C13—C16—H16A	109.5
C6—C7—H7A	120.7	C13—C16—H16B	109.5
C8—C7—H7A	120.7	H16A—C16—H16B	109.5
N2—C8—C7	124.68 (10)	C13—C16—H16C	109.5
N2—C8—C9	114.68 (10)	H16A—C16—H16C	109.5
C7—C8—C9	120.63 (11)	H16B—C16—H16C	109.5
O2—C9—O1	124.63 (11)	H1WB—O1WB—H2WB	115.4
O2—C9—C8	124.61 (11)	H1WB—O1WB—H1WA	109.0
O1—C9—C8	110.76 (10)	H2WB—O1WB—H1WA	83.0
O1—C10—C11	106.88 (10)	H1WB—O1WB—H2WA	97.1
O1—C10—H10A	110.3	H1WA—O1WB—H2WA	102.7
C11—C10—H10A	110.3	H1WB—O1WA—H2WB	116.1
O1—C10—H10B	110.3	H1WB—O1WA—H1WA	115.9
C11—C10—H10B	110.3	H2WB—O1WA—H1WA	93.6
H10A—C10—H10B	108.6	H1WB—O1WA—H2WA	98.9
C10—C11—H11A	109.5	H1WA—O1WA—H2WA	118.4
C10—C11—H11B	109.5	O2Wⁱ—O2W—H1W2	81.5
H11A—C11—H11B	109.5

C8—N2—C1—N1	−179.96 (10)	C1—N2—C8—C7	−0.23 (17)
C8—N2—C1—C5	0.51 (16)	C1—N2—C8—C9	−179.34 (10)
C2—N1—C1—N2	−177.43 (10)	C6—C7—C8—N2	0.02 (18)
C2—N1—C1—C5	2.10 (17)	C6—C7—C8—C9	179.08 (10)
C1—N1—C2—N3	178.37 (10)	C10—O1—C9—O2	−0.67 (17)
C1—N1—C2—C3	−1.63 (17)	C10—O1—C9—C8	179.55 (9)
C12—N3—C2—N1	175.30 (12)	N2—C8—C9—O2	3.82 (17)
C12—N3—C2—C3	−4.7 (2)	C7—C8—C9—O2	−175.33 (12)
N1—C2—C3—C4	0.06 (18)	N2—C8—C9—O1	−176.40 (10)
N3—C2—C3—C4	−179.94 (11)	C7—C8—C9—O1	4.45 (15)
C2—C3—C4—C5	1.06 (18)	C9—O1—C10—C11	−172.58 (10)
N2—C1—C5—C6	−0.57 (17)	C2—N3—C12—O3	4.9 (2)
N1—C1—C5—C6	179.93 (10)	C2—N3—C12—C13	−172.27 (12)
N2—C1—C5—C4	178.48 (10)	O3—C12—C13—C16	26.19 (17)
N1—C1—C5—C4	−1.02 (17)	N3—C12—C13—C16	−156.66 (11)
C3—C4—C5—C6	178.40 (12)	O3—C12—C13—C15	147.54 (14)
C3—C4—C5—C1	−0.60 (17)	N3—C12—C13—C15	−35.32 (15)
C1—C5—C6—C7	0.34 (17)	O3—C12—C13—C14	−91.47 (15)
C4—C5—C6—C7	−178.65 (11)	N3—C12—C13—C14	85.68 (13)
C5—C6—C7—C8	−0.08 (17)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···O2W	0.85	2.39	3.051 (2)	135
N3—H1N3···O1WBⁱ	0.85	2.40	3.095 (3)	140
O1WB—H2WB···N2	0.86	2.26	3.077 (3)	160
O2W—H1W2···N1ⁱ	0.83	2.13	2.948 (2)	167
C3—H3A···O3	0.93	2.23	2.8230 (17)	121

Symmetry code: (i) −x, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₉N₃O₃·1.5H₂O
M_r	656.73
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	30.7759 (7), 7.2406 (2), 16.9271 (4)
β (°)	120.009 (1)
V (Å³)	3266.32 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.41 × 0.31 × 0.24

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.960, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	16624, 3753, 3156
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.108, 1.04
No. of reflections	3753
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.23

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
N3—H1N3···O2W	0.85	2.39	3.051 (2)	135
N3—H1N3···O1WBⁱ	0.85	2.40	3.095 (3)	140
O1WB—H2WB···N2	0.86	2.26	3.077 (3)	160
O2W—H1W2···N1ⁱ	0.83	2.13	2.948 (2)	167
C3—H3A···O3	0.93	2.23	2.8230 (17)	121

Symmetry code: (i) −x, y, −z+1/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship. SG and AH thank the CSIR [No. 01 (2292)/09/EMR-II], Government of India, for financial support.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Goswami, S. & Hazra, A. (2009). Chem. Lett. 38, 484–490. Web of Science CrossRef CAS Google Scholar
Li, D. Z., Li, Y., Chen, X. G., Zhu, C. G., Yang, J., Liu, H. Y. & Pan, X. D. (2007). Chin. Chem. Lett. 18, 1335–1338. CrossRef CAS Google Scholar
Listvan, V. N., Listvan, V. V. & Shekel, A. N. (2002). Chem. Heterocycl. Compd, 38, 1480–1483. 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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